James Buckhouse, founder of the Sequoia Creative Lab and a self-described “storyteller”, will be the first to tell you that that the word “storytelling” is a total buzzword.

“There’s no faster way to make people actively ignore you and hate you for no good reason than to tell them you’re a storyteller,” he says. “The story is what motivates us. The story is what helps us find meaning in not just our momentary actions, but in our long-term actions.”

At Intercom, we’ve written at length about designing products through a Jobs-to-be-Done lens, where you start by identifying the jobs your product needs to solve for your users. Buckhouse, on the other hand, starts with a story, by taking design, engineering, and product through a storyboarding process he adapted from a previous life as an animator at Dreamworks.

I’ve always thought of design as this long, interwoven story of a person’s daily life, and a person’s every moment. And the things that we make are multipliers, augmentations to that.

In the latest episode of the Inside Intercom podcast, Stewart Scott-Curran, who heads up brand design at Intercom, talks to James about the role of storytelling in product design. James shares his framework for teams to uncover their own product story, advice for working with founders, how to listen, and much more.

Click the play button to listen below or head to our blog for the full transcript.

Intercom makes messaging apps for businesses that help them understand and talk to customers.

Want to hear weekly conversations with practitioners from the worlds of product management, design, startups and marketing? Click below to subscribe to our podcast, or visit our blog Inside Intercom to see all of our past episodes and transcripts.

Sequoia’s James Buckhouse on why product design should start with a story was originally published in Inside Intercom on Medium, where people are continuing the conversation by highlighting and responding to this story.

Process for a product team can be suffocating, or process can be liberating. And no process at all? Well that’s fun for maybe a week or two before everything starts to fall apart.

Our team has done a lot of work over the last while reflecting and improving on how we build product. Our goal was to arrive at the minimal process that gives teams a framework to plan and structure their time, and most importantly, to prioritise and make the best tradeoffs.

Previously, we thought about building product over three timelines — 6 weeks, 6 months and 6 years (which Paul catchily referred to as the “666 mindset”). But now the 6 month roadmap is no more. The one constant, the core of that framework that we’re doubling down on, is the 6 week cycle. Here’s how we think about it, and what it looks like in practice.

Why the 6 month timeframe didn’t work

The simple truth for any product team is this: the further out you plan, the more suspect the commitments become.

Making far-out planning commitments with your product team actually has compound negative interest:

• Your team spends a too much time planning upfront. Planning is necessary, but great teams want to be building. So much time spent planning means the job has become less fun.
• No matter how hard you try, your plans are still largely fiction. So the team feels either scared (because you were really ambitious) or de-motivated (because it’s too cautious), and likely de-energised.
• Teams outside R&D will soon realise that the plans aren’t reliable, so R&D loses credibility.
• Your plans feel like strait-jackets that you’re constantly having to re-adjust, but from which you’re never able to actually break free.

So instead of using a 6 month cycle, now we keep our roadmaps unbound by time: they’re simply the next 5 projects that a team is going to work on, in prioritized order. That’s it.

It might take the team two months to finish those 5 projects, or it could take two quarters. Doesn’t matter. This simple list of 5 projects unlocks the next step — the 6 week cycle.

6 week cycles are about execution

With a list of projects to work on next, teams can focus exclusively on what they can accomplish in the next 6 weeks. This is actually a big deal. You no longer have to juggle strategy and execution in a single conversation, which is deceptively head-wrecking. Your brain will thank you.

Here’s how the 6 week cycle works in a little more detail.

Goals, not plans

We don’t optimize for detailed planning. Instead we focus on the goals for the cycle. Every 6 weeks, each team proposes a handful of goals for what they want to accomplish that cycle. Because you only have to project 6 weeks out, you don’t need a detailed plan to have high confidence in your goals. This keeps it lightweight.

Then the team nominates one primary goal. This is the goal for which you’ll sacrifice all others to hit when you need to adapt to changing circumstances. Agreeing this upfront makes the typically hard decisions that arise around week 4 (“Crap, Project A is taking longer than expected. What should we do?”) refreshingly easy (“Actually, it’s clear. Let’s stop work on Project B and commit everyone to A.”)

Our main goals are usually about releasing an improvement to all customers. And secondary goals often focus on releasing to beta. We optimize for visible progress for all customers.

And we include candidate goals as well. These are goals we considered but rejected. This helps us think about what we’re choosing not to do this cycle. It’s important to be explicit about this.

Then we pull all these together in a single spreadsheet, which everyone has access to. Here’s the summary tab of our R&D goal spreadsheet, showing an overview of each team’s main goal:

Accountability matters

Each goal of the 6 week cycle is specific and measurable, and teams are held accountable for them, particularly the primary goal. This requires a subtle balance — you don’t want teams to become cautious, otherwise they won’t hit any goal. So we don’t expect perfection. Missing goals happens. But teams should feel good about what they’re committing to — that it’s achievable and something they’d feel proud about delivering in 6 weeks. It should hurt to miss your goals.

They’re not delivery cycles

Our planning and commitment timeframe is 6 weeks, but we don’t use that to artificially constrain projects. One project might be designed, built, and released in just a couple weeks, while others will span across a couple of cycles. You should be releasing product the whole way through a cycle. And sometimes you’ll hit your main goal in week 3 or 4. That’s all totally fine. 6 weeks is simply our planning and commitment cadence. It’s our structure to help give the teams the right level of predictability and foresight.

6 weeks is the Goldilocks of timeframes — just right

Building good software is really hard. You need your processes to support you, not pull you down. We’ve found the 6 week cycle does just that. It helps your team fight for meaningful goals, and gives you flexibility within 6 weeks to adjust and adapt to the inherent uncertainty of shipping product. It strikes the balance between making commitments your team believes in, and giving your team a wide-enough window to use their creativity to actually make it happen.

The team at Basecamp have a different model behind it, but still ultimately share a conviction that 6 weeks works well for building product. That makes us even more confident that 6 weeks is, well, just right.

You should give it a try too.

Written by Brian Donohue, Group Product Manager at Intercom. Illustration by Ryan Troyford. This post first appeared on the Inside Intercom blog, where we regularly share our thoughts on startups, company culture, product strategy and design.

Intercom makes messaging apps for businesses that help them understand and talk to customers..

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6 weeks: why it’s the Goldilocks of product timeframes was originally published in Inside Intercom on Medium, where people are continuing the conversation by highlighting and responding to this story.

When we revamped the Inside Intercom blog, we wanted to provide readers with a truly editorial experience — something you would get from reading a high quality editorial publication, and not a run of the mill corporate blog.

Key to that was working with a wide array of talented illustrators and artists from around the world to help bring our posts to life. Regular readers have come to love these pieces, and how they creatively interpret blog posts on topics as varied as how to track the right company metrics to tips on providing great customer support.

We asked Stewart Scott-Curran, head honcho at the Intercom Brand Studio to take us behind the scenes on the process.

How do you find the illustrators that contribute to the Inside Intercom blog?

I’m always on the lookout for people whose style would be a good fit for us and I keep a roster of illustrators whose work I know, or who I’ve come across on Dribble or Behance. Sometimes an illustration in a publication like The New York Times, Wired or Slate will catch my eye and I’ll find out who worked on it and check them out.

Do you look for any particular style or approach?

The only filter I have is, “Does this look like it has been created by a human being?”

We tend to stay away from super clean, vector illustrations that you see in a lot of other places. We try to keep it a lot more organic, loose and expressive.

One of the opportunities we had when we started thinking about these images was taking a more editorial approach. Much like the design of the blog itself, there’s no reason why it shouldn’t look editorial, like something you might see in Fast Company, and not just another company tech blog.

What’s the process to get from commissioned to finished piece?

We generally just send the illustrator a draft of the blog post and let them have at it. We keep it pretty simple, and tell them to feel free to interpret the post in any way they want.

It’s okay to get a little bit weird, or a little bit abstract, and to have some fun with it.

The best ones are the ones that don’t translate the content of the post too literally, that are little bit left of field. We don’t get prescriptive, we like to give the illustrators we work with a lot of freedom. Occasionally, if we come across someone who has done lots of work in different styles, we’ll reference one or two of of their previous pieces as something we feel would work for us.

What advice would you give to illustrators looking to catch your eye?

We’re always looking for new contributors. I’m happy for anyone to reach out to me on Twitter if they think their work would be a good fit, or reach out by sending us a message through Intercom.

Intercom makes messaging apps for businesses that help them understand and talk to customers. Check out more illustrators on the Inside Intercom blog, where we regularly share our thoughts on startups, company culture, product strategy and design.

Behind the scenes on the Inside Intercom illustrations was originally published in Inside Intercom on Medium, where people are continuing the conversation by highlighting and responding to this story.

In a simple design, every element has to pull its own weight. A messaging app — no matter what frills it’s decorated with — should be a simple design. And its simplest elements are words.

Even the simplest design carries the weight of expectations for how it ought to work — and when its elements don’t work as expected, people react. Strongly.

Last year, the words we added to the Intercom Messenger interface generated some intense reactions to the most minute details of grammar and phrasing. As our product manager, Brian, said to me: at least we know our words are being read.

Getting under the skin of those reactions and the expectations behind them has changed how we think about and write for our Messenger. And as we’ve written before: when you change how you write for a product, you change how the product is perceived. You change expectations.

Interface vs conversation

Messaging apps — puppy filters aside — are usually designed for one thing: to let you talk to someone as naturally as you would if they were in the room with you.

If the internet has proven anything, it’s that people feel very strongly about what they feel is ‘correct’ grammar.

This simplicity is core to messaging’s power and popularity. That’s why consumer messengers like WhatsApp spread so easily across all demographics: they were an easy leap from natural conversation, and from the native messengers everyone already had in their phones. A product like Whatsapp allows you to do more without having to learn more.

Our own Messenger took that simplicity to B2C conversations, so that businesses and their customers could message each other directly.

While business messaging is still essentially the same simple platform, it has the potential to be more socially complex: that’s because the participants in the conversation have specific roles, and specific jobs they need to do.

Giving stage directions

A messaging app isn’t primarily a set of screens and interactions. Underneath that, its parts are pretty much like the parts of a script: there are speaking roles, and stage directions.

There are two speaking roles for human beings in our Messenger:

• The customer asking a question
• The team member answering the question

There’s also one non-human speaking role. It’s carried out in the form of a bot.

The other parts of the interface are the stage directions — messages from Intercom that appear in the flow of conversation, and in the frame of the app itself, that provide instructions and context, so the human participants know what’s going on, and can act accordingly.

Talking without body language

When you have a conversation with someone in the real world, you usually know who you’re talking to. If only from body language, you have a sense of your role in the conversation and your relationship to the other participant.

That knowledge affects what you say and how you say it. It also affects your expectations of how the other participant will reply.

Weird things can happen when speaking roles are unclear. Just a few weeks ago, we spotted this tweet from one of our customers:

Here, a real human using Intercom to talk to a customer was assumed to be a bot: an example of our social expectations of a conversation evolving to keep pace with technology.

Expectations play a big role in how any conversation evolves. And relationships evolve through conversation. If the reply we receive in a conversation with a business doesn’t match our expectations of how the conversation should go, it changes how we feel about that business.

That means one thing is critical when designing for conversations: everyone needs to understand who’s speaking at all times.

Leading by example

Remember our non-human speaking role? Our “bot” in Intercom — though it’s designed more like a courier than a full participant in the conversation — is meant to deliver information to the customer and carry data back to the business.

Last year, we gave two key jobs to our bot:

1. To let users know when they can expect a reply
2. If they’re not logged in, ask for a way to notify them when their reply arrives

These jobs came with two sets of expectations:

• That “live chat” is always immediate
• That chats in the Messenger are sent by a real person

How soon is now

People often have a “live chat” expectation when they use messaging apps on websites and apps, by which I mean they expect a relatively immediate, call-center-like experience. But like any text message, our Messenger is designed to be asynchronous — it’s not always live. The primary job is to get customers an answer, but they don’t necessarily have to wait around to get it.

So we wanted our bot to deliver a message along these lines, on behalf of the absent team or teammate:

“Brian will reply soon — but you don’t have to wait around.”

The key word here is “soon”.

That word is polarising: we knew from user testing that people interpret it to mean either “right now” (aka “this is live chat”) or “in a long time” (aka “I may never get a reply”). So we wanted to avoid it.

Content design rule #1: Don’t use the word ‘soon’.

When trust is a product job

There’s a great deal of trust at play in our Messenger: trust between Intercom and the businesses that use it, and trust between them and their customers.

Changing the text wasn’t a simple matter of brainstorming different copy.

When we deliver messages to do a specific job, like ask for contact details, we have to speak on behalf of a business. This can have surprising complications: one of which is knowing the gender of the precise person we’re speaking for: the member of the team who’ll reply to a customer.

We wanted to refer to that teammate like this: “This person will reply as soon as they can”. As the bot was doing the speaking, it had to refer to this person with a pronoun: ‘she’, ‘he’ or ‘they’.

But as we don’t know the person’s gender — that’s not data Intercom asks for from teammates using our product — we couldn’t say “he” or “she”. So while we didn’t want to say “Brian will reply soon”, we also couldn’t say: “Brian will reply as soon as he can.”

In this context, these words — pronouns and adverbs — are load-bearing. They’re individual words that perform a job.

• The pronoun makes it clear that the message is not from that teammate, but from a bot speaking on their behalf.
• The adverb manages that time expectation, as best a single word or phrase can do.

We were constrained on both counts.

Now, the singular pronoun “they” was 2015’s word of the year — so it was technically correct to use it. So we released a fix with “Brian will reply as soon as they can”.

But if the internet has proven anything, it’s that people feel very strongly about what they feel is “correct” grammar. Businesses felt it was incorrect to use a gender neutral singular “they”, and it didn’t always translate well into other languages.

That meant we’d failed in our primary job of communicating on each business’s behalf in a way that felt right to those businesses.

One job at a time, one word at a time

Changing the text wasn’t a simple matter of brainstorming different copy. We had to rethink our priorities, and reconsider the jobs we were trying to get this bot to perform.

Here’s what we shipped: “Don’t miss Brian’s reply: Get notified by email.”

We realised we had to set one job — setting reply expectations — aside, and focus on motivating customers to leave their contact details. That was the primary job, and trying to get one message to do two jobs had failed.

It took a lot of work to get to those 8 simple words: getting to the right phrasing for a specific job means having absolute clarity about what you want to communicate, and getting rid of anything that competes with that job.

By switching our focus to the job that meant a customer would have a better chance of getting their answer, we could communicate more clearly.

Content design rule #2: Be careful your sentences don’t shoulder too large a burden: one job per sentence is enough.

Getting closer to simple

Everything we’ve learned about our Messenger in the past year has shown that tiny changes have a big impact. Every word we change and every new approach we take to a particular problem has a monumental effect disproportionate to its size. A messenger is a human space, and our customers respond to it as such — with a strong sense of ownership and of what feels right.

So we take care over these elements; we sweat the details down to every pronoun. With every detail, we push our Messenger design forward, and see how much weight a simple design can really carry. Turns out: a lot. If you get the balance right.

This post first appeared on the Inside Intercom blog, where we regularly share our thoughts on startups, company culture, product strategy and design. Illustration by Adam Avery.

Intercom makes messaging apps for businesses that help them understand and talk to customers.

Interested in more articles about language in design? We’ve got your covered.

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How soon is now? Discovering the many jobs of language in design was originally published in Inside Intercom on Medium, where people are continuing the conversation by highlighting and responding to this story.

“I sometimes laugh because here I am, sitting, looking at Excel spreadsheets and talking and worrying about margins. How have I become that person?”

Like many creatives, Tina Roth Eisenberg, aka Swiss Miss, didn’t think sales spreadsheets would become part of her day-to-day.

But the New York-based entrepreneur and blogger has managed to turn not one but five side projects into successful, profitable businesses. First, there’s her popular design blog, Swiss Miss, which averages a million unique monthly visitors and cemented Tina as a beloved tastemaker. Then there’s Tattly, her design-led temporary tattoo company; her breakfast lecture series Creative Mornings, which now has more than 160 chapters around the world and Friends, a collaborative co-working space.

Each of these business evolved organically out of things that piqued Tina’s interest, or things that frustrated her, and each has taught her lessons about how to be a designer-turned-founder.

Becoming a better salesperson is something you can learn, and it doesn’t have to be a dirty word if you’re a creative.

In an interview with Stewart Scott-Curran, who heads up brand design at Intercom, she shared her advice for designers-turned-startup-founders, her tips for juggling multiple projects, and the role community can play in inspiring great work.

Click the play button to listen below, head to our blog for a transcript, or keep reading for some highlights.

1. Everyone can learn to become more sales driven

Becoming a better salesperson is something you can learn, and it doesn’t have to be a dirty word if you’re a creative. “When you’re a sales-driven company, at the end of the day, even if you sell artistic things, you need to care about your margins and the sales channels,” Tina say. Though she admits she’s “not a salesperson at heart”, running a sales-driven company — even one as quirky and creative as Tattly — forced her to start caring more about the sales process. “I had to learn and embrace sales as an art form.”

2. Make innocence a competitive advantage

Entering an industry as a novice can feel daunting, but it also means you question things that seasoned industry veterans wouldn’t think to. “It’s incredibly refreshing when you start a business with such innocence and enthusiasm like I did and then automatically bring a breath of fresh air to an industry that others would never even dare to do.”

3. Mix up your network

Tina attributes a lot of her success to making an effort to work with people in industries other than her own. “You benefit when you surround yourself with people that are equally driven, creative, but from different industries,” she says.

“Find a group of people that has really high standards in their work and that complement you in some way. I have become so much better at everything I do and have set my bar so much higher and my goals have changed because of the people that I surrounded myself with.”

4. Design your way to success

Graphic designers have a distinct advantage starting businesses, as they can quickly create a cohesive, polished looking brand identity. “The second day I was in business with Tattly the Tate Modern shop buyer called and said, ‘How long have you been in business? You have such a great brand.’ I was sitting there thinking, my God, we’re two days old,” recalls Tina. “Just because I was a graphic designer I was able to make it look professional right out of the gate.”

Intercom makes messaging apps for businesses that help them understand and talk to customers.

Want to hear weekly conversations with practitioners from the worlds of product management, design, startups and marketing? Click below to subscribe to our podcast, or visit our the Inside Intercom blog for key takeaways and transcripts.

Tina Roth Eisenberg on 4 things designers-turned-startup-founders need to know was originally published in Inside Intercom on Medium, where people are continuing the conversation by highlighting and responding to this story.

As an Engineering Manager it’s not always obvious where to allocate time for maximum impact.

Time spent in 1:1 discussion with my direct reports is the highest leverage time in my calendar and it’s the de-facto place I go to every week to see where I can make a difference. For 30 minutes of time I get the opportunity to amplify the work of somebody on my team by an order of magnitude for a sustained period. Multiply that out by my team size and compound that over 52 to get a feel for the kind of impact effective 1:1’s can have on team success over 12 months.

This week I will spend 35% of my time in 1:1 meetings. When I started allocating this kind of time I was deeply dissatisfied with the return on investment. Sometimes I’d leave happy, only later to discover that my directions weren’t clearly understood. Sometimes I’d forget what I’d said last week. Sometimes I’d spent 30 minutes shooting the shit. Sometimes we’d rehash things discussed in planning. Sometimes we were talking at a time when we really should have been doing.

Over the past few months fueled by ideas from people like Andy Grove and Jeff Caselden I’ve been tinkering to try improve the impact of my 1:1 time. Here are some things I’ve found to be important.

Know why you’re meeting

You need buy in from your report that the 1:1 meeting will not only be a valuable use of her time but an essential component to her success at your company. You should spend at least the first couple of 1:1 sessions imparting your philosophy. I find it useful to appeal to the self interest of the team member at first. Let them know what you can offer them directly. Typically this means career development, growth opportunities and guidance. The goal here is to get your team member to take the 1:1 slot seriously — and not consider it an interruption to otherwise more important things. You might need to repeat this exercise many times.

When two people chat, each person will leave with their own perspective on what that conversation was about.

If you’re a brand new manager, on a new team, or new to the company it might be worth inverting this completely to start. Let them know how they can help you so that you can eventually help them.

Clarify ownership

Ownership of 1:1s and associated work is a little tricky. One non-negotiable is that the time belongs first and foremost to the person you’re managing. Regardless of what you want to talk about, always give your report first choice on the agenda. This means they should turn up with an agenda — I think that’s also important. Chatting for three minutes about what to chat about is a really good use of the first three minutes.

I personally prefer to own the scheduling and notes by default. This can be flexible though, as long as things are clear. As with much management work, identifying ownership and expectations up front is a useful exercise in avoiding misspent time.

Scope the meeting

You want to be really open initially, so avoid explicit scoping in the first few meetings.

1:1s are the right place to talk about career goals, expectations and to give performance feedback.

They are the right place to gather feedback on you, others or the company and to get in tune with satisfaction levels. They are one setting in which you can identify potential blockers or ways in which you can help as a manager.

They are the wrong place to discover project status, to understand what that person is currently working on, or to assign ownership on roadmap work.

You should discover project state and assign ownership to work elsewhere. If these things come up they should be directly related to the experience of the problem rather than a process of discovery for you. They might want or need help or direction on something. In that case it’s in scope.

A large part of your role as manager is identifying the right people to solve a problem and linking those people together.

You’ll probably come across things that are legitimately in scope for somebody to raise with you, but are out of scope for you to deal with directly. If there’s a difficult personal problem, it’s worth understanding where you can help, where the limits of your remit and ability to help are and what options you might have to get additional forms of support — either for you or for your report.

Be prepared

People complain a lot about meetings. Unfortunately I haven’t discovered a more high bandwidth, high leverage way of sharing knowledge than a face to face meeting. What I think actually bothers people is bad meetings. Bad meetings are the bar across the industry right now. There are a few reasons for that. One is lack of preparation, which I genuinely don’t understand. There’s no excuse: Get your shit together and get it done on time. If for a genuine reason you’re not prepared, cancel the meeting. Don’t go through the motions.

As a manager, safety is your responsibility.

To help with preparation there are two note sets that I maintain per person on my team. The first is a feedback diary. A simple bank of short, constructive and positive feedback that I note down over the week. The second is meeting notes. I jot down what we chatted about in bullet point form and identify actions as well as owners for those actions. A good cadence on this means 1:1 prep requires very little overhead. I typically spend 10 minutes per 1:1 sorting this stuff out.

There are some 1:1s that require more than 10 minutes preparation. In difficult performance review situations I like to spend at least 30 minutes with a peer running through what I want to say and how I’m going to say it, to sanity check my position and identify flaws in my reasoning. I’ve found this really useful.

More often than not it’s the thing you don’t identify up front that becomes the primary issue, but the act of running through things with somebody else crystallises my thinking and makes it easier for me to think on the fly. I think of this as a kind of code review for managers. Not only a chance to leverage the collective experience but a chance to share context and understanding across the management team.

Follow up

When two people chat each person will leave with their own perspective on what that conversation was about. Depending on many things, those two individuals who think they are completely aligned will in reality range from somewhat aligned to totally misaligned.

To help us get in sync, at the end of each 1:1 I jot down the key points of the discussion as I understood them, note down the key next steps and the owners of those and send that email to my team member. For a small investment of time this has some great upsides, including:

• I crystalise my understanding of what was important about that conversation by writing it down.
• I sanity check this against the other person’s understanding.
• I give the other person the opportunity to clarify my misunderstanding or to identify their own.
• What’s expected of everyone next is crystal clear.
• Over time I build a great set of useful notes.

Create and maintain a safe environment

It’s incredibly difficult to have a successful team if your team members don’t trust you. It’s incredibly difficult for them to trust you if you don’t create a safe environment for them to express themselves. The most insightful and useful 1:1 conversations happen when everyone feels safe. It’s not easy to create safety, especially when the stakes are high and people are out of their comfort zones. There’s a whole book on this. I boil it down to:

• Let people talk, in whatever manner they want, using whatever natural tone or language that allows them to express themselves. This might not be enjoyable for you, but, remember, it’s not about you.
• If people close off, get defensive or nervous looking they’re probably feeling unsafe. You should pay really close attention and step back at this point. Anything talked about from here on will be low value until you’re both feeling safe again.
• Unless you get direct and explicit agreement otherwise, what’s said in 1:1s should remain in 1:1s. If Mary expresses a weak desire to move teams and without permission you tell John this and John mentions it to Mary and Peter then you need to find a new team for Mary. Mary’s going to find it very hard to trust you with much from then on. Game over.

It’s worth remembering that as a manager safety is your responsibility. It might even be your primary concern.

I’ve been in 1:1s where managers have lost their temper, where they have burst into soliloquy or pontification at the slightest sense of disagreement. When that happens my back goes up. Good luck understanding what I’m really thinking from that point on. I try to remember this when working with my team.

In the aftermath of a 1:1 gone bad I’ve heard managers pawn off the seriousness of the situation with “My intentions were good”. It’s very hard to prove what your intentions were, even to yourself. Also, nobody cares about your intentions. People don’t experience intentions they experience outcomes.

If you mistime a tackle in rugby and end up around the opposing player’s neck it’s your fault. Your intentions are irrelevant because the consequences for the player are severe. Even if your intentions were golden you’re leaving the field of play and your teammates behind for 10 minutes, or 10 weeks, depending on the outcome. Team member safety is your responsibility — no excuses. Create and maintain a safe environment.

Schedule effectively — but be flexible

By default I schedule 30 minute meetings with five minutes either side for prep, notes and follow up, so 40 mins per 1:1. I fix this time on a weekly cadence creating an open opportunity to chat and a predictable rhythm. That’s my starting position. Sticking to this schedule as much as possible and giving enough notice at a reschedule is really important. People that rely on you like you to be predictable.

I’ve found it more important, however, to be really flexible. If you’re only starting to draw out the really useful feedback at minute 25, or something of critical importance comes up in minute 27 the absolute worst thing you can do is indicate you’ve something else to be doing next and there’s a chance you’ll be late. This will be a judgement call but my point here is don’t live by the clock. There are some places you’ll go in 1:1s where you’ll want to stay for an extended period right then and if you interrupt that flow you’ll literally never get back there. So be flexible. Whoever you’ve scheduled next will appreciate this when it’s their turn.

Another reason the bar for meeting quality in our industry is so low is timing of meetings. It’s naive to schedule a meeting, get a ‘yes’ in reply and then to assume that ‘yes’ will continue to apply right up to the start of the meeting.

There are so many reasons why exactly now might not be a good time. I manage engineers. There’s a point of flow in an engineer’s day that they spend most of the rest of the day chasing. It’s the uber productive time where they’re in deep work. It’s the place where they add millions of dollars of value. There is a study that shows when engineers move from that place it takes 20 minutes to get back there. This assumes they will get back there. In practice and with even the best of intentions there might be two hours of elapsed time before that 20 minute process starts. It might be home time then. As a manager, flexibility is part of your job description. I like to open each 1:1 with “Is now still a good time?”. It’s really important to create a predictable schedule but it’s even more important not to be beholden to it.

Adapt your style

I’m inclined to avoid more specific recommendations like “listen more than you talk” or “always ask another question”. In different situations with different people applying these kind of principles has ended up with me listening very attentively to complete silence or irritating an engineer by coming across as a professional socratic questioner and little else. The key point here is be present, use your judgement and adapt your style to the person, the context and the general mood.

Learning and iterating

Over the past few months I’ve found that by following these guidelines:

• Performance reviews are easier.
• Joint understanding of expectations of me are becoming clearer.
• Joint understanding of expectations of my reports are becoming clearer.
• Post-feedback behavioural changes are more noticeable.
• Post-feedback tasks are getting done.
• Indirect feedback on my performance as a manager has become more positive.

There are always areas to improve, but I’ve found the below to be common challenges to watch out for:

• Concurrent note taking and active listening is challenging.
• As an alignment mechanism, emails aren’t perfect as they can often go unread. I haven’t explicitly measured this, but I would guess that the read rate on my follow up emails can be 50–60%.
• Maintaining safety is a difficult art. Sometimes concentrating on total safety can dull the outcomes of otherwise interesting conversations. This is probably because I’m not practiced enough at it yet and it’s tricky to learn something new and engage at full-tilt at the same time. To mitigate for now I’m investing in my apology mechanism 😀
• I mostly take 10 minutes extra per engineer for prep, notes and follow up. Sometimes it takes me 20 minutes. Scaled up across seven engineers weekly this is a significant difference. I’m exploring ways to make this more efficient and ensure alignment post-meeting.
• I still haven’t figured out if it’s better to batch 1:1s together in an afternoon to minimise context switching or to spread them out over a few afternoons to optimise for energy. A “1:1 day” sounds like a good idea, but sometimes I’m lacking in energy at the end of the day, which is bad news for the team member in the 4.30pm slot.

Chatting to other engineering managers around Intercom it’s clear that there is no single effective shape or system for 1:1s. Certain formats and systems work better for different people — I understand and learn by reading and writing notes, but others might find this torturous.

What is clear is that 1:1 time is the most valuable time a manager has to have impact. Whatever mechanism or system you use it’s worth understanding if you’re using that time optimally. Since this time is so high-leverage, even minor tweaks can yield significant, compounding results.

This post first appeared on the Inside Intercom blog, where we regularly share our thoughts on startups, company culture, product strategy and design. Illustration by Andrew Kolb.

Intercom makes messaging apps for businesses that help them understand and talk to customers.

Interested in more articles on work, startup life and management? We’ve got you covered.

• People leave managers, not companies. Don't let that manager be you. - Inside Intercom
• To perform at your best, focus on goals not tasks - Inside Intercom
• Finding your way from maker to manager - Inside Intercom

How to run 1:1 meetings that work for 2 was originally published in Inside Intercom on Medium, where people are continuing the conversation by highlighting and responding to this story.

Building a successful product means getting good at saying no. But exactly how do you say it? What if you’re on the front line, representing your company’s product decisions, how do you deliver that news successfully?

Working as part of the Customer Support team at Intercom, I’ve experienced first hand just how tricky this can be. Ultimately, the information that you’re about to share is not going to be what the customer wants to hear. However, there are a few key things that can help you make that “no” a bit more palatable for your customers.

Say no with a why

Like any negative conversation in life, context is key. If you can explain why you’re saying no, it’s an easier pill for your customer to swallow. Without it, customers feel entitled to be angry, upset and disappointed. With context, they can still feel all these things but deep down they’ll know they’re a little less entitled to.

A common consolation is the knowledge that something isn’t a mistake, but a deliberate decision.

Customers feel frustrated when they believe a sloppy oversight has led to a feature they would love being overlooked. The simple reassurance that this decision is tied to your company’s end goals and is in line with your overall mission can completely change how the news is received. Never underestimate the power of why.

A good relationship between support and product teams can really help provide this context and solidify the why. At Intercom, the Customer Support team members will regularly jump into product team Slack channels and run through logic of decisions with engineers to make sure we fully grasp the details of any given decision. Having that open line of communication means you can get that extra sliver of insight and say no with even more detail and confidence.

Don’t change your tone

When you’re chatting with customers about how great your product is and how much they love your newest feature it’s easy to be personal and for conversations to be all sunshine and gifs. But something I’ve seen happen to lots of my teammates is the second they have to have an awkward or undesirable conversation with a customer, they stiffen up and their language completely changes. When the conversation takes a turn for the worse it’s easy to let all that personality go and default to formal speak. But this is when being personal is most important.

People are afraid of conflict and are uncomfortable saying no on behalf of their company, so they become overly formal and in turn, somewhat robotic.

From the frustrated customer’s perspective, a stiff “no” reply can be interpreted as you not having any empathy for their situation and simply parroting off a stock company line.

Remain friendly and personal when saying no. Resist the urge to hide behind formal language and try to continue to be yourself as much as possible. If in doubt, ask yourself if you’d use the same language to explain the situation to a friend or colleague. If it would feel weird speaking to them that way, then don’t speak that way to your customer.

Involve the customer in the solution

Things go wrong and mistakes happen. Funky and frustrating bugs crop up and customers are negatively affected. We’d all love to have a clear and solid explanation for every issue customers face but the reality is sometimes that just isn’t possible.

If, like Intercom, most of your customers are running businesses themselves, appeal to that business sense.

Involving the customer in the resolution helps them empathize with you.

It also helps you get a fuller picture of the fallout and allows you to appreciate and understand why and how they were affected. Asking things like, “What do you think would be a fair compensation to get us past this?” or offering a solution and then asking “How does that sound to you?” can really bring the customer into the situation and help them feel empowered in the resolution.

Sometimes a hard line has to be taken and you need to push back of course, but when you involve the customer in finding the solution it can be the catalyst for them taking a more pragmatic approach to the entire situation.

Focus on the job to be done, not the no

At Intercom, we really discourage our Customer Support team from simply saying, “You can’t do that at the minute, but we’ll pass it on as a feature request” to our customers. Granted, sometimes that is the response that makes most sense but typically we try and dig a little deeper.

It’s far better to try and move the focus off the feature a customer is asking for and on to what they’re actually trying to achieve. Ask a few more probing questions to find out exactly what their end goal is. Best case scenario, you’ll know a work-around. Worst case scenario, you now have extra context to pass on to your product team.

Breaking up is ok too

The idea of telling a customer that it’s okay not to continue using your product and to perhaps check out other options instead can be a really tricky thing to get your head around.

There are reasons why you built your product the way you did and it would be silly to expect that to align with the needs and wants of every customer and company out there.

Nobody wants a frustrated, disillusioned customer who constantly contacts your support team because they’re struggling to use your product in a way that it’s simply not designed to work.

At Intercom, if we know a customer is paying us good money we want them to love our product and really feel the value from every penny of their monthly subscription. There will be ups and downs during their lifetime as an Intercom customer, and those things we can get around.

However, if what the customer wants to do is something that our product fundamentally is not built to do, then they’re never going to feel happy and satisfied and we’re never going to fully ‘get around’ it.

They’re never going to feel they’ve gotten bang for their buck and they’re not going to enjoy using our product. In those cases we’ll be sad to part ways but we’ll definitely suggest it if we know it’s best.

Have empathy for both sides

Always strive to show empathy to your customers but never to the point that you end up throwing your engineering or product team under the bus. It’s fine to agree that you’d also love to see a certain feature added.

But try balancing that with a shout out to some of the cool features that have been recently shipped or improved on. This can help hammer home the deliberate nature of how your team builds and can remind the customer that you didn’t just forget or overlook building the features they’d like, you simply decided that others took priority for now.

This is another example of the benefit of having a strong relationship between support and product teams.

Being close to your product team, knowing and appreciating what they’re working on, and working hard on, means you prevent your customer support team from developing a biased perspective with one-directional empathy.

Say no with confidence

Being able to say no and say it with confidence is certainly not an easy skill to master. It takes time and practice and even the most seasoned pro will get it wrong from time to time. However, if you have a solid and deep understanding of your company’s core values and can genuinely say that you’re on board with them, the odds of a successful no conversation will be significantly higher.

Written by Sharon Moorhouse, Customer Support Lead at Intercom. Illustration by James Heimer. This post first appeared on the Inside Intercom blog, where we regularly share our thoughts on startups, company culture, product strategy and design.

Intercom makes messaging apps for businesses that help them understand and talk to customers.

Interested in learning more about providing great customer support? Download your copy of our latest book, Intercom on Customer Support today.

How do you say no to customers? was originally published in Inside Intercom on Medium, where people are continuing the conversation by highlighting and responding to this story.

A fact of startup life is that no matter what team you work on, you’re guaranteed to run into problems you get stuck on.

The challenge is deciding how much time to spend on each problem. Should I try to debug a problem until it’s solved, or should I ask for help when I’m stuck?

Ask yourself: Am I really the best person to solve this problem?

By using the 15 Minute Rule, everyone on your team learns the value of self-sufficiency, but it forces them to reach for the life raft when they really need it.

I was taught the simple rule by Jeff (our Director of Customer Support here at Intercom), when I was a junior customer support engineer. If I was stuck on a particular customer problem, he told me to first take 15 minutes to try find the answer before looking for help. If I still didn’t have an answer after 15 minutes, I had to ask him for help.

The 15 Minute Rule
Take 15 minutes to solve the problem any way you can. However, if you don’t have an answer after 15 minutes, you must ask someone.

You must try for yourself

It wasn’t that Jeff didn’t want to help me — he did. But if I kept escalating bugs without even trying to figure it out, I never would have learned how to solve problems for myself.

Taking 15 minutes teaches you the skill of not only knowing what to look for, but how to look for it.

One of the most valuable skills in any customer support or engineering team is navigating internal codebases, documentation and knowing that, more often than not, the answer is there if you take the time to look for it.

Just as importantly, it means that when you do ask for help, you’re at least armed with the full context of the problem at hand. You might have tried looking in the codebase, searched old conversations, searched Slack, and searched through the internal documentation and still come up short. But 90% of the time you’ll be coming with some valuable threads of information for the person who’s helping you out — so you can both solve the problem quicker.

But you also must ask for help

But there are situations when you cannot unblock yourself in 15 minutes, or even if you looked all day. In these scenarios, the 15 Minute Rule forces you to ask for help.

It’s way too easy to disappear down the rabbit hole trying to solve problems; you need to take a step back and ask yourself: “Am I really the best person to solve this problem?”

The fact is — your time is expensive. It might feel good to learn things the hard way — you’ll build valuable skills along the way — but there are no prizes for spending 3 hours on a problem someone else could have solved in 10 minutes.

How the 15 Minute Rule can help the whole team

For anyone building a customer support team (or engineering team for that matter), the 15 Minute Rule has real benefits:

• New hires are taught self-reliance
• But have an all important safety net if they get stuck
• New hires can get mentored by senior members and see the logic of how they solve problems
• Senior members get to informally review and give feedback on the team’s work
• Support staff are upskilled while customers don’t have to wait too long for answers

Even though I no longer work as an engineer (or even know where most of our documentation lives 😀 ), the 15 Minute Rule is still something I use regularly. It teaches you to respect your colleagues’ time, but not to be afraid to get help when you really need it. So give it a try, and let us know if it works for you in the comments.

Written by Martin Brennan, Customer Support Lead at Intercom. Illustration by Shawna X. This post first appeared on the Inside Intercom blog, where we regularly share our thoughts on startups, company culture, product strategy and design.

Intercom makes messaging apps for businesses that help them understand and talk to customers.

Interested in more posts on how to make startup life better? We’ve got you covered.

• To perform at your best, focus on goals not tasks - Inside Intercom
• How to run 1:1 meetings that work for 2 - Inside Intercom
• Finding your way from maker to manager - Inside Intercom

Know when to ask for help with the 15 Minute Rule was originally published in Inside Intercom on Medium, where people are continuing the conversation by highlighting and responding to this story.

Let me tell you a story.

Once upon a time, there was a brave and handsome prince. He passed all his prince school exams, expertly avoided any encounters with dragons, and lived happily ever after.

Not much of a story, right? Where is the adventure, the struggle? The allies, the enemies, the ordeals and the rewards?

Yet this is exactly the kind of story countless startups are telling: All the shiny, happy, good stuff, none of the guts and gore that make for a compelling read. And in doing so, they’re missing a huge opportunity to connect with their audience in an authentic way.

“If you look at storytelling over centuries, every story has a story arc,” says Lucy Allen, General Manager and Head of Bay Area at Edelman, a leading global communications and PR firm. “You can’t have a story arc without there being some kind of hero struggle, an obstacle for the protagonist to overcome. If you don’t have the arc, you just have a flat line. That’s not exciting for anybody.”

In today’s society, we have to earn attention and credibility. It can’t be just bought or demanded.

Lucy’s spent the past two decades working with technology companies of all sizes — from young startups to the likes of SAP and Adobe — to build their profile and share their stories. She recently spoke to Jennifer Kutz, who heads up communications at Intercom, about how startups can get better at telling their story and connecting with their audience, and shared insights on how PR needs change as you grow.

Click the play button to listen below, head to our blog for a transcript, or keep reading for some highlights.

Sowing the seeds of a rock solid PR strategy

• Know when to start. Unless you’re in stealth mode for very specific reasons, the time is now — Lucy maintains that even if you’re not at the stage where you want to be promoting yourself, you should be thinking about building your reputation and earning credibility. “In today’s society, we have to earn attention and credibility. It can’t be just bought or demanded,” she says. “Every organization needs some level of “PR”, because everybody needs to earn the right kind of attention or credibility at some point.”
• Pitch smarter. When pitching a story to a media outlet, think about their readers and goals — not yours. “Business media typically writes about just two things: people and money. If your story doesn’t have a strong human element and can’t talk about the people whose lives it’s affecting, or it doesn’t talk about money in a way that’s meaningful to individuals, to consumers, or that shows how you are moving markets, then it probably doesn’t have the right ingredients for a news story.” Consider how what you’re doing plays into wider industry trends, and what impact you will have beyond the four walls of your company.
• Do you pass the “so what” test? If what you’re sharing doesn’t somehow surprise the reader or tell them something they didn’t already know, don’t be surprised if it fails to make an impact. “News is the psychology of the unexpected,” says Lucy. “If your news story doesn’t pass the “so what?” test then it’s not a news story.”
• Share the rough and the smooth. Sharing what you’ve learned is key to building trust and credibility and, usually, that starts with a personal journey. “A startup may not have vast numbers of customers or great big partner ecosystem to talk about yet. But what you do have is your founders,” says Lucy. “What are some of the challenges that you’ve faced? That will resonate much more.”

The role of PR as you grow

As your company grows and changes, so too do your PR needs.

Series A: Getting attention early on: At this stage, your focus is most likely on getting credibility and understanding of your technology. “Getting attention early on is all about making sure there’s an understanding with your very specific target audiences of what it is you’re trying to communicate,” says Lucy. “That may be best done internally, because those are the people who have an understanding of the technology or the products or the proposition. That said, that’s also the phase where you have a small team. You may not have a marketer or a communications expert in-house, so you many need to turn to somebody externally to help you take that message and communicate it.”

B and C rounds: Focusing on revenue generation: “Almost everything you’re doing here is geared around lead generation, customers, partners,” explains Lucy. “The type of PR that you do will change and it needs to be tied in very tightly to your content marketing and lead generation programs.” You may still be able to do the majority of your PR in-house, but as your needs become more complex or specialist, you might need to explore bringing in an agency.

D and E rounds: Expansion stage: At this stage you might already have begun transitioning from a single product to a multi-product company and widening your focus into different markets, which is when the safety net of working with somebody who has done it before will prove crucial. “You may be looking to expand internationally. You may be thinking about a liquidity event,” says Lucy. “All of those things require not only additional expertise, but you also need to work with somebody who’s done that before.”

Intercom makes messaging apps for businesses that help them understand and talk to customers.

Want to hear weekly conversations with practitioners from the worlds of product management, design, startups and marketing? Click below to subscribe to our podcast, or visit our the Inside Intercom blog for key takeaways and transcripts.

Why you need to make failure part of your PR plan was originally published in Inside Intercom on Medium, where people are continuing the conversation by highlighting and responding to this story.

Words in a product evolve. They start with the people who first invent the product and name its parts.

They change when new teammates bring in fresh influences. And they change again when they need to communicate to a new audience. All that change happens incrementally, word by word.

It reminds me of the Ship of Theseus, a 2,500-year-old thought experiment about the nature of identity. If you change every plank in a ship while it’s on its journey, is it still the same ship when it returns?

For products made of words and pixels, words are at least 50 percent of the ship.

Words also guide what we build. We invent words to describe new features, and those choices are often an informal choice: a buzzword we use to give a loose shape to what we’re building.

But naming can be serious business.

While there’s an entire corner of the branding industry devoted to inventing product names, it’s the names of individual elements — features and objects within a system — that can have unpredictable impact.

Take the name “page”. That name gave presence to “places on the internet” before we knew what those places would become. And we designed for that word and the metaphor it represented. We were so used to thinking of a page as a fixed thing that it took years to break free of that constraint.

Names unconsciously influence how we think about what we design, and working titles can quickly become real titles with unrealised baggage.

Shipping content strategy

Taking charge of language is a challenge for any company, but none more so than a growing startup. The evolution of a product dialect can cause silos to build up between teams who call things by different names, take features down detours when they’re not well described, and worst of all, create inconsistencies in product UI. That’s why you’ll often find different names for the same thing in a product, or different tones of voice everywhere.

At Intercom, content strategy has one core job: to evolve our dialect, at every level, from something organic to something intentional; to make our UI — and how we talk ourselves — consistent and coherent.

Here’s how we’ve begun to move things forward, plank by plank.

Uncovering our building blocks

We’ve categorised every visible word in Intercom’s product. Objects, views, people, actions: these are all different parts of the system with different roles to play, and some are more essential and persistent than others.

The output of this is a taxonomy itself: a model that gives us consistency and control over how we describe each part of our product, and clarifies the relationships between those parts. And doing that work of classification and definition also produced our glossary of terms used in Intercom.

Mapping our mental models

Before we could define the words in the glossary, we needed to investigate where each one originated and how they were now used.

That meant interviewing people from every team in Intercom, taking note of the words they naturally use to describe the product and how they relate those words to each other — their internal sense of how our ship was built.

The answer to this was that of any company: we’re a team with different jobs and mindsets. People who see things visually, systematically, or linguistically have different ways of seeing the world and so use different words to describe it.

What we found was, like all great research, totally unsurprising once we’d discovered it: we each used the words that suited our own jobs and goals.

Our differences aren’t a failure, they’re an asset — as long as we’re aware of them, and they don’t get in the way of us understanding each other, or our customers understanding us.

Tracking our way to clear principles

Choosing names and writing UI content can feel temporal and subjective. To remove the vagaries of mood and subjectivity, it’s good to write down some principles, even if you end up evolving them later. They shouldn’t be a straitjacket — new principles will emerge, others will go into storage.

But choosing principles relevant to right now is the best way to ensure your future creative choices are clear to yourself and everyone else.

These are the three principles we started with:

1. The product speaks naturally, as people speak
2. The product speaks directly to the user (but never for the user)
3. The product helps the user, guiding them through complex ideas

Why we’ve arrived here now

When’s the best time for a startup to start thinking about product content strategy? Should you start crafting your product voice this way from the beginning?

On the one hand — though it can feel like a luxury — content work is never easy, so it’s wise to start considering it early on.

But in another sense, that work is at its most illuminating and transformative when it’s a little bit anthropological — when there’s an organic voice there to discover.

Rather than applying an artificial idea of what the ‘right’ voice, structures and words might be, which can easily lead to a product that sounds just like everything else, try finding the patterns already there, and bringing them to light.

Written by Elizabeth McGuane, Content Strategy Lead at Intercom. This post first appeared on the Inside Intercom blog, where we regularly share our thoughts on startups, company culture, product strategy and design.

Intercom makes messaging apps for businesses that help them understand and talk to customers.

Interested in reading more about content strategy for startups? Check out Elizabeth’s other posts:

• The best name for your bot is no name at all - Inside Intercom
• How soon is now? Discovering the many jobs of language in design - Inside Intercom
• What content can learn from product development - Inside Intercom

How the words you use build your product was originally published in Inside Intercom on Medium, where people are continuing the conversation by highlighting and responding to this story.