Lessons in leadership from running a startup
There aren’t many advantages to a global pandemic suddenly shutting down your business.
But there are some.
An enforced slowdown
At the start of 2020, I was running as fast as I could.
My startup Sn-ap had raised a funding round in the first half of 2019. Startups operate on 18-month funding cycles, so we would need to raise again in summer of 2020. That meant we had to achieve a whole bunch of proof points, very quickly.
Suddenly, in March 2020, everything stopped.
My business (a digital platform that aggregated people who wanted to make long-distance leisure journeys into groups to be fulfilled by independent coach operators) was about the most Covid-sensitive you could imagine. In effect, lockdown was a ban.
I spent nine months attempting to save the business (including an ill-fated pivot into providing coach travel for construction sites: an area of the economy still open) and then accepted that it was over. So, I made the team redundant.
By the start of 2021, I was on my own.
Time to think
Like most of us running at top speed, I hadn’t previously had much time to stop and think.
When most of us leave a position of leadership, it’s normally because we’re moving onto a new, even more exciting opportunity. We’re focused on what comes next.
But I had this rare opportunity of having my leadership suddenly guillotined. I joined Transport for London later in 2021, but the winter lockdown gave me plenty of time to reflect.
I sat down and wrote a document called “Useful lessons learned on running teams”, which I’ve looked at periodically ever since, and which I share with you now*.
* I’m not actually sharing what I wrote word for word. It’s in incomprehensible note form as was only intended for my eyes.
What had gone well
Honesty
One of the things leading a startup teaches you is that you have to be honest, and honesty gets the best from people.
I met startup founders that attempted to dissemble and hide from their teams the true state of things when their businesses were struggling. It simply added a stress burden to the founder while creating a misalignment between the team’s work and the company’s needs. If the building is burning down, you don’t want people acting like it’s simply that the air con is broken.
I took an early decision that I would always be very open with my team about what was going well and what was not. In 2019, we had a major funding crisis. The round we were raising proved difficult. When we finally closed the deal, we had got to the point of having already started clearing computers out of the office.
Raising the cash took all my time. The team knew exactly the state of things (including the fact that it was perfectly possible they would be unemployed next month). As a result, while I was out dealing with the money, they were working in the most wonderfully self-directed way building new features. The launch of one of them, a crowd-sourcing platform grandiosely called “Republic of Snap”, was the thing that got a crucial wavering investor over the line.
It's hard to come up with illustrations for a post on leadership. So here's a beer mat advertising Republic of Snap.
Values
One of the bits of advice I got when setting up Sn-ap was to be very intentional early on as to what our company’s values would be and to communicate them clearly.
Corporate values can seem a bit bollocks but it’s hugely important to be clear how we work here. I really wish I could show you the various materials we created to communicate our values at Sn-ap but I lost access to the Sn-ap drive when I handed the keys to the administrator in 2021. But they were good.
But it wasn’t the quality of the graphics that mattered, it was the fact that we talked about them. I presented them to new starters and made sure they were a part of our language. This meant that, by and large, they were adhered to and actually reflected how we behaved. However, a lesson learned was also that they need to be enforced and seen to be enforced. There were a few moments when I could have done that better, being honest.
Pre-mortem / success / failure:
Embracing failure is such an important part of success. One of the things we did well was creating a culture in which we could openly talk about both successes and failures. Sharing these was a part of our weekly all-hands meeting. A particularly useful format is the Pre-mortem, a structured thinking session which imagines a project has already ended in failure. You then do a “post-mortem” on that failure, speaking in the past tense. It’s remarkable how easy it is to talk through the things that led to that failure when you’re doing a Pre-mortem, even though often you’re describing things you’re actually doing right now.
Failure is too often not part of our language. But a startup is never more than a few months from failure, so it’s much easier to make it part of everyday life. Corporates often feel the need to be glossy and positive with talk of failure pushed under the carpet. This is a mistake.
Communication
You can’t over-communicate. You really can’t.
One of the successes was my weekly voicecast. Recognising that my team was distributed across multiple cities in the UK, I started recording a weekly voice note to my team. This was great as it dealt with the problem that everyone wants more communication than they get and no one wants an extra meeting and another email.
Because it was a voice note, I could be open, honest and nuanced in a way that is tricky in an email (nuance in an email is tough: honesty can backfire) but because it wasn’t a meeting, people could listen at a time that suited them. It was never compulsory to listen but many people did - often while making a cup of tea.
We also did a lot of experimentation on how to do a start-of-day check-in. It felt really important that we connected as a team at the start of every day but starting the day with a meeting felt like a thoroughly bad idea. We therefore used a Chrome browswer plug-in called Loom to do a really quick video check-in at the start of each day. That worked.
In addition, we had a weekly all-hands meeting. This meeting was focused on a (honest!) business update, sharing success and sharing failures across the team. It was relatively informal and it didn’t matter if someone couldn’t make it.
Tools
There were a whole bunch of digital tools that we found invaluable. That feels like a separate post.
Still struggling for illustrations. So here are some Sn-ap branded cupcakes...
What had not gone well
Empowerment
I’ve described elsewhere on this blog the critical importance of empowered teams to get things done. And I had personally seen how effective the culture of empowerment at Chiltern Railways had made me.
But I really struggled to get it right at Sn-ap.
I believed in it, and self-identified as an empowering leader.
So it was a bit of a shock when my team came to me and said “Thomas, we don’t feel empowered”.
As soon as they said it, I realised it was true.
In my defence, empowering as a startup leader is particularly hard. When you start, the business is literally just you. So you have to make every decision. As the team builds, you have to very consciously step away from decisions that you previously had taken. It’s a similar challenge, incidentally, to being promoted within a team. It’s a challenge I seemed to be failing.
So I decided to ask the team to run a series of workshops on the subject of empowerment, exploring what it meant, what good looks like and, crucially, what they need from me.
They did an amazing job: exploring different approaches taken in different types of organisation, and clearly setting out how we needed to work in future. Many of the approaches I teach through the Freewheeling business had their origins in this workshop.
However, I still hadn’t got it quite nailed.
A few weeks later, two team members came up with a proposal. They presented it perfectly: with a clear, concise paper backed up with evidence. It fulfilled the Amazon principles (of a “crisp paper and messy meeting”) perfectly.
However, it was not a good proposal. As in, while the proposal was presented well, it was not a good idea. Indeed, it was very clear from the data that the evidence was that we should not do what they suggested.
I took a decision that we would not do it. They were very upset. They had worked hard on it and they had become personally committed. It was actually a very difficult meeting.
Afterwards, I spoke to my coach*. I told him I’d had a really “bad meeting”. I explained that I was trying to empower my team and yet, when they’d come to me with a proposal that they passionately believed in, I’d had to overrule them because the evidence did not support them.
* like athletes, leaders need coaches
My coach picked up on my use of the words “bad meeting”. He asked why I’d categorised it as “bad”. I explained that it was because they were really upset, and it was me that had made them upset. He (with the patience of a primary school teacher explaining something to a particularly stupid child) explained that it was actually a “good” meeting. I had made a clear decision and prevented a harmful proposal from being actioned.
At last, I understood what empowerment looked like. It meant that teams should be given maximum autonomy to deliver the business’s outcome goals. I should not get involved. But when decisions needed to be escalated to me (such as, in this case, because it was a fundamental change in approach or because of a conflict between teams or because more money was needed), then I should be swiftly decisive - focused entirely and exclusively on the good of the business.
Still struggling for images. Here are some empty desks at our first co-working space
My job
I don’t mean that my job went badly: I think I did pretty well, all told. Most startups fail and few succeed. I’ll never know if we would have succeeded but being killed by Covid as opposed to by our own actions is a good death, as they go.
No, what I mean by this is that I didn’t realise what my role actually was while I was doing it.
It took me a time to realise what my job, as CEO, actually entailed. As CEO, there are only three areas that are proactively MY responsibility:
Ensure clear objectives for the business
Recruit the best possible people
Make sure we have money
That’s it. Nothing else.
Everything else should be led by the team. I should be ready to course-correct or respond to escalations but all my proactive actions should be on goals, people and money.
My job is to make sure that everyone is absolutely clear on the goals (hence my weekly voicecast) and how their role fits in. One of my ‘lessons’ notes says “Be really explicit on goals and repeat frequently. Have clear, visual plans”. Too many of us, as leaders, spend too much time DOING things that are actually someone else’s job. That’s a double-bad. Firstly, we’re not doing our job. Secondly, we’re undermining one of our team members.
We should be spending that time finding endless different ways to make sure our teams understand the goals. Really understand them. Because if they do, they will do the DOING that we - if we’re honest - enjoy stealing from them. But it’s far, far more efficient to be a proper enabler of a team than to do the doing yourself.
I didn’t do a terrible job of this but, because of my background, I tended to spend lots of time fiddling with our pricing model. With hindsight, this was not a good use of my time.
Things that went well that I wish I’d done more
Structured feedback sessions
So many of the things that are best for you in life don’t appeal. Most of us prefer chocolate to broccoli or watching telly to exercise.
So it is with team meetings. The kinds of team meetings we feel comfortable with are the corporate equivalent to snuggling up on the sofa watching Love It or List it. They’re easy but not useful.
But the best kinds of team meetings are effortful.
One that we did - but not frequently enough - was structured feedback sessions.
These need plenty of wicketrolling in advance: you can’t just spring them on people.
But done well, they are invaluable.
The way they work is that around six people sit in a circle. You go round the table, focusing feedback on one person at a time. Each person feeds back to that person one thing you do well, one you do badly and one thing you can do for me.
This may sound terrifying.
And you need to make sure everyone approaches it the right way. But it’s not as scary as it sounds.
Yes, each person ends up with six bits of ‘negative’ feedback. But they also end up with six bits of positive feedback. And they get six bits of constructive, helpful advice.
I never regretted running these sessions, so why didn’t I do so more often?
Saying “Thank You”
I bought a set of postcards and used these to send handwritten Thank You notes. They were always appreciated. (Given the state of my handwriting, I’m not sure anyone actually deciphered what they said but it’s the thought that counts, right?)
I also used the online gifting platform Huggg to buy surprise ‘thank you’ gifts for key moments.
But when I looked back in the cold light of a Covid lockdown day, could I have done more of this? Yes. Should I? Yes.
Writing and posting individual, personal thank you notes to the team was time-consuming. But it was also valuable. So why didn't I do it more often?
In Conclusion
Leading a startup is an exercise in pure leadership. If you’re appointed to a leadership position in an established organisation, you inherit a team and you recruit in the name of an established brand.
As a startup founder, you start with nothing. I genuinely can think of no better leadership training that building a team from scratch.
The experiences I've shared—honesty with your team, embracing both successes and failures, the struggle to empower others, and understanding your true role as a leader—are not just reflections of what happened but guideposts for what can be done better.
They are lessons I took into my role in TfL (it’s for my team there to judge how well I did) and which I now teach in my role at Freewheeling. I’ve found the lessons valuable; I hope you do too.
How can I help you?
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TAKE ACTION!
Entrepreneurial organisations are biased to action.
If you’re a leader:
Be Transparent: Regularly communicate both successes and challenges with your team to align efforts and foster trust. Don’t shield your team from the truth, especially in tough times.
Define and Reinforce Values: Clearly articulate your company’s values and integrate them into daily operations. Regularly revisit these values to ensure they are lived, not just stated.
Embrace and Analyse Failure: Create a culture where failure is openly discussed and used as a learning tool. Consider implementing “pre-mortem” sessions to anticipate and mitigate potential risks.
Empower Your Team: Delegate decision-making authority and encourage autonomy, but be ready to step in decisively when necessary. Balance empowerment with clear, outcome-focused leadership.
Communicate Effectively: You can’t over-communicate (you really can’t!). Use multiple communication methods, like voice notes or video check-ins, to keep your team informed and engaged without overwhelming them with meetings.
Focus on Your Core Responsibilities: Prioritise setting clear objectives, recruiting the right people, and ensuring financial stability. That’s it! Resist the urge to micromanage and instead enable your team to execute.
Conduct Regular Feedback Sessions: Implement structured feedback sessions to provide constructive input and foster continuous improvement within your team.
Show Appreciation: Regularly acknowledge and thank your team members for their contributions. Small gestures, like handwritten notes or surprise gifts, can go a long way in boosting morale.
For Team Members:
Seek Honesty and Transparency: Encourage open communication with your leaders about the state of the business and your role in it. Understand the bigger picture to align your efforts with the company’s goals.
Align with Company Values: Ensure your daily actions reflect the company’s stated values. Engage with leadership to clarify any ambiguities and live these values in your work.
Embrace Learning from Failures: Participate actively in discussions about what’s going well and what’s not. Use these insights to adapt and improve your approach to your work.
Take Ownership: Look for opportunities to take initiative and contribute to decision-making. Understand that empowerment comes with the responsibility to act in the best interest of the business.
Be Open to Feedback: Approach structured feedback sessions with an open mind. Use the feedback to grow personally and professionally. Your boss will be nervous doing this: say ‘thank you’ and show you found it valuable.
Express Gratitude: Acknowledge your colleagues’ efforts and successes. A culture of appreciation isn’t just the leader’s responsibility—it’s something everyone can contribute to.
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