Why Your Startup Needs a Team Coach

People problems are inevitable and you’re probably ill equipped to deal with them on your own

Hannah Donovan
Aug 5 · 13 min read

There is a popular myth that coaches are for weak leaders who need help. This couldn’t be further from the truth, coaching helps strong leaders optimize what they already do well and strengthen what they don’t.

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Why I hired a coach

I met Karina when we were both at Twitter. Karina helped me with some pretty serious issues on the Vine team, and during that time I realize how critical it is to have the support of a coach when you’re leading and executing. three key reasons:

1. Your industry is always changing

Change is going to happen at a different rate for everyone, and mindset change is an inevitable part of any creative act. Creativity (what some companies call “innovation” is dynamic, not static. It is uncomfortable, it is messy, it happens in fits and starts. It requires personal growth and change.Whether you are leading organizational change (like a business turnaround), or simply getting folks excited about the next feature on the roadmap and needing to make adjustments for the next quarter, making things is a dynamic state. If your company stops changing, it will probably soon be out of business.

Most people don’t like change. Change is scary. Change in mindset and culture is the hardest to implement and the most critical for business success. Plus, as a founder, you probably don’t have time to focus on this, it’s just a thing that plagues you when you’re trying to fall asleep at night “ugh, I just need to get people to X! Why can’t we Y faster? Do they have their brains switched on to Z?

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My focus is on strategy and execution. As a design founder, I want to be involved in what we’re making as well as how it’s going to work and look. You may not be a designer, but there’s probably something you really care about in your business that is your superpower and you stay in the weeds on. It’s probably something you built your business on — brand, sales, technology etc. But, as an execution-focused leader, you don’t have time to make sure everyone is on the bus, everyone’s got the map, everyone is going in the right direction etc. You probably have one opportunity to tell them “this is where we’re going, here’s the map, let’s go!” And you’re off. But, If you run off and someone got left at the bus stop, it can create conflict. I think of this a bit like software updates. I’m updating my hypotheses on our work weekly, I need to make sure everyone else’s brain got the update, and that their system is running the latest version. If we get a few versions out of sync with each other, that’s where problems start to happen. Of course, there are plenty of ways to do this as a leader and you should definitely use all your tools to do so, but it can really speed you up to have a partner who is focused on it.

2. Your team is cross functional

I knew from previous experience working with machine learning that it is really really hard to get different types of people to talk together, let alone work together. (See our post on how to collaborate without killing each other, haha!) As a designer. I’ve worked hard to build my knowledge of machine learning and algorithms. I can keep pace with scientists in a conversation and follow without the conversation going over my head. I can read papers on new methods and think critically about how we could build on them to create new features — not just from a “what if?” perspective, but from a genuine “is this possible for us right now?” perspective. This takes time, and takes a lot of practice and patience to learn how to talk to scientists. I still don’t always get it right! I knew from past failures that if we wanted to build a truly cross-functional high performing team that was a genuine blend of art and science in our approach to our work, it was going to take a lot of coaching the humans, that in itself is change.

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3. Your team is diverse

If you didn’t all graduate from the same school, if you don’t all look the same, you’re going to naturally use different language and have ways of thinking. This is important, a diverse team is a strong team! But, you’re probably going to need help genuinely connecting with each other and including each other in the act of creation. A coach can really help here too!

In summary, get a coach if:

  1. You work in a dynamic field that requires constant learning, growth and change to succeed
  2. You’re building a cross functional team where people of different disciplines need to collaborate effectively
  3. You’re creating a diverse team with people from different backgrounds

Types of Coaching

There are three key types of coaching. Karina helps the TRASH team with all three. It sounds like a lot, but remember, if you really want to get shit done, this is going to support your mindset, your team’s mindset and the structures that both support and limit those mindsets.

  1. Exec coaching: this is probably what comes to mind when you think of coaching, 1:1 sessions with leaders to help them be more effective. This is good, and can be particularly important when leaders are going through a stressful situation, but it’s one sided. The coach will only ever hear the leader’s account of things, and therefore can only be as effective as the leader’s self-awareness.
  2. Team coaching: this is observing the team and assessing team and individual performance, coaching the team to be more effective in group settings (like a planning session) or meeting 1:1 with team members to help them be more effective. For a coach to help with the team, it’s critical that they have access to all aspects of what the team is doing: key meetings and key tools (like Slack) so that they can observe and debug issues.
  3. Business coaching: This is going a level deeper to assess the systems the humans are operating in. Are the systems enabling the humans or are they getting in the way? For example, how are meetings timed throughout the week and handled? How are hiring and on-boarding supporting and enabling the vision? For this, the coach needs access and ability to create change within the structures of the organization overall.

The difference between coaching and advising

This was one of the most surprising things I learned from Karina. A great team coach knows how to be both a coach and an advisor. Similar to how the best designers can think about both the big-picture as well as the details, a team coach should be able to wear two hats:

The coach hat: this is about knowing the right question to ask, not about having the right answer. A coach tries to ask the right questions so the person can see the answer that is already inside of them. A coach draws this out not by telling them out to do it, but by being a true sounding board. It requires getting people comfortable and open to facing themselves.

The advisor hat: this is about having the answers. With the advisor hat on, your team coach is providing advice, giving solutions, for example: “here is what I would do in this situation”. This is much more hands on and direct. The coach needs to have built confidence with the team to be able to do this.

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A lot of consultants can give advice and think they can coach. A lot of coaches are good at asking questions but don’t know how to think like an operator. You want someone who can do both.

How to do it on a budget

You’re probably thinking: this sounds awesome, but how the hell am I going to carve out budget for this? How am I going to tell my investors? This seems impossible or like it’s only for privileged and well-funded startups. No.

Like anything, the devil is in the details. If you’re serious about success and genuinely think this can help you get there, you need to advocate for this — like I’m doing right now. You know your company better than your investors.

There are a few ways to make this work:

  • Offer equity. Like any position, having skin in the game is going to make your coach more engaged (more on this below)
  • Make it part time: you probably don’t need a coach full time if you’re an early stage startup, so make it a part-time staff position
  • Make it part of a larger role: when Karina first started working with us, she also did all the company operations. In start-ups you wear many hats.

Equity is also important for both business coaching and wearing the advisor hat. It’s a different level of investment for your team coach. If you want a coach that is more involved on the business side (not just the team side) you have to be able to offer enough time for them to have less clients.

The job description

On a typical day, Karina is doing a combination of:

  1. Engaging in active meetings: in some this might be a light observation because someone else is running them, other times it might be facilitating the entire thing (for example a team retrospective or a user research focus group). This includes observing group conversations on slack, noticing automated messages like software deploys, reporting and logs etc.
  2. Assessing existing processes: process is just another word for habit. Are the team habits the right ones still, or do they need updating? Karina is constantly looking for ways to make modifications so the team can be more efficient.
  3. Doing 1:1s with team members: what is happening with their potential, are they motivated? Why or why not? My guess is as a founder, you don’t have much time for this. Simply being there for people so they can have a checkin if they need it can alleviate a lot of stress and catch problems before they happen.
  4. Sharing insights with the founders: Key updates, observations, things I may not notice that are coming down the pike and I’m going to have to deal with. It’s a coach’s job to close the feedback loop on their learnings.

Why incremental change is key

At TRASH we implement change regularly. Trying new processes is easy, because we’ve all developed that muscle. If we don’t like it, we know we can throw it out next week because we’re dynamic. If you don’t have someone who can do this for you (and my guess is it’s not your top priority as a founder), then you may not change as often as you need to and this can be a big difference in being a successful startup as well as the happiness of your employees. Having someone who can make incremental change on a weekly basis in a safe way that doesn’t freak people out or interrupt their flow, you don’t have to make big changes that cause you to slow down so you can speed up again, or worse, piss people off and cause attrition.

The most challenging part of the job

Karina says that balancing the dire timeline of a startup with the needs of the founders and the needs of the team is the hardest part of her job. Operating with the sense of urgency that is necessary in a startup makes you want to take short cuts. From a people standpoint, those shortcuts can often demotivate or disrupt teams. However, those short cuts are necessary for survival, so finding a balance is always a challenge.

A Practical example: the coach sees a conflict happening where the team members involved don’t have the skillset to resolve it. It’s slowing them down and impacting product delivery. The coach wants to pump the breaks, back up a bit, restructure the project to create lasting change for those team members. But, the startup is on a tight schedule, so they have to optimize and figure it out in the moment which might mean coming back to clean up the mess later. This is also known as building the plane while you fly it, everyone’s doing it.

Working with founders is also challenging. They are highly ambitious people who have a lot of drive and vision. They are super focused on execution and results. Figuring out how to help them without dampening them can be a real challenge. The magic that comes from their charisma, passion and drive is value to the team, but their blessing can also be their curse.

A practical example: the founder has very clear vision on where the company needs to go and very clear expectations of the team. If the team can’t completely see that vision for some reason, they can’t latch on to it, and the expectations wont be met. The founder will be frustrated. “Why can’t you see this is important!?” The coach may want to get that founder to pull back and slow down to re-explain to the team, but this may lead them to question and doubt themselves. That’s where the coach can pick up the team and pull them forward to where they need to be instead of pulling the leader back. (In a larger co it would be a different strategy obviously, because of different market drivers and goals).

The space this brings a founder

The team coach is a support system to the founder to make sure the team is activated and working to their full potential. It’s a peace of mind for me to know that if people are having problems, they aren’t festering until I find them, that I’ve got someone watching my back while I close the next deal, come up with the UI for an innovative feature, or whatever else I need to be doing.

With her coach hat on, Karina will observe problems. With her advisor hat on she’ll build systems to solve those problems and be directive about implementing them. Then with her coach hat, she’ll make sure the team sticks to the system to be successful. I’m so grateful to have a partner like that.

How you can do this too

So, you want to hire a coach. How the hell do you do that?

How to hire a coach

  1. Get a referral: talk to other founders and investors and see if they are working with anyone. A lot of founders don’t like to talk about this —because of the “I don’t need a coach“ myth that this is a sign of weakness, so you may need to dig one on one, not in a public forum like Twitter, though that can work too! A Google search is risky, there are a lot of people selling snake oil. A referrals is the best way.
  2. Interview them for the coach hat and the advisor hat. Ideally, they’ve worked as an operator in a big co. The same way investors are usually more helpful if they have an operator skillset, so is a coach, since everything is about execution in a startup. Having a coach that hasn’t just been a coach is important. This will be a good indicator they can wear the advisor hat too and give you directives when you need it.
  3. See if they engage with your unique issues: listen carefully to see if they try to sell you on their “framework”. Similar to how creative agencies will charge you thousands for their specific creative process (that is probably really an intern doing a google image search for their creative director), frameworks can be very recipe driven as opposed to truly engaging with what your business needs. Of course, some method is necessary, definitely take this with a grain of salt, not all frameworks are an up-sell.
  4. Get references: Ask them if you can talk to some of their clients. A coach who is not comfortable with that is a no-go.
  5. See if there is vibe: like a therapist, you have to feel really comfortable with this person. You need to have good energy. It helps to go on a walk or meet for coffee or a meal so you can put your antennae out for this in a more casual setting. Ultimately, you want a partner. Someone who can really get to know you, understand you and motivate you. They should be there to help you when you need it, being a founder is lonely and hard.
  6. Look for complementary skills: similar to the Hollywood approach of finding an assistant, find someone who is a bit opposite of you (ie. if you say yes to too many things, get someone who can say no for you; if you have a tough personality, get someone who can be charming), will help you be an awesome duo. I know I struggle with patience, I want everything done yesterday. Karina has the patience I lack.

Key characteristics of a coach

  1. Humble curiosity: a coach must have the humility to understand that no matter how much experience they have, they have’t been on your journey
  2. Patience: change takes time. Every human is going to have their own journey with changing their mindset, and the coach must be patient
  3. Sense of humor: coaches can’t take themselves too seriously. There are going to be moments where it’s awkward af, and humor diffuses that.

How to determine the engagement

When you’re hiring a coach, ask them about their book of clients. If they’re a single person company and they have 10–20 clients, they’re not going to be able to offer you as much coaching. If you want exec coaching, team coaching and business coaching they’ll need more time for you.

If you can offer equity, financial incentives or benefits for that person to have less clients, then they can more easily be in your day to day. That’s where the real value comes in, being in meetings, observing communication styles, where abnormalities are happening. Being present and seeing the behaviors. If you can invite a coach in like that, they can have constant context. If you’re not doing that, there is still value but it’s different.

What about coaching in big companies?

It looks very similar but the scope and scale varies. If you’re inside an enterprise context, there is a lot of value for a coach to help with things like your operating model, org design, organizational systems etc. Instead of being involved at the individual level with team members, the coach is usually working more closely with leadership. It’s also probably going to be heavier on the advisor hat than the coach hat. Leading a large transformation effort is going to be more operational. It will require designing the change, helping the team implement, and then coaching them on sticking to it.

The model here is: Build—Operate — Transfer

Have a coach help build the change with you, operate it with the team, and then transfer all the knowledge and move on to the next problem with the humans! They will never run out of work to do.

Further reading:
The Five Dysfunctions of a Team: A Leadership Fable
Humble Inquiry: The Gentle Art of Asking Instead of Telling

TRASH

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