After Product Issue #3

Welcome back to After Product.

In this edition, we’ve been educated on the world of coaching with Seb Agertoft. Probably a career path that wouldn’t have occurred to many of us - enjoy!

Whilst you do, don’t forget to share After Product with your Product pals - ta 🙏

To get started, how did you get into Product?

The honest take there is I basically got into it because I didn’t want to be a strategy consultant or investment banker.

I studied Economics & Management at Oxford, and there was some statistic that the majority of grads who did my course went on to one of the top consultancies or investment banks. And I just didn’t think either of those things were for me.

I’ve always had a slight entrepreneurial streak and an interest in tinkering with product and tech. So I took a job in a small fintech start-up as a Product Analyst (although that’s not what it was called).

I started getting more responsibility and moved into Product Management, and learned it on the job. It was very much a stumble-and-fall into Product as opposed to a deliberate trajectory.

What came next?

I’ve spent a good chunk of my career trying to learn new skills and find routes to fast growth.

So from that first Fintech, I went to Qubit. It was very well funded, but also a pretty chaotic start-up environment. I had a lot of fun there, learned a lot, and met plenty of people I’m still friends with today. I also learned a lot of lessons about how not to do things.

From there, I moved to eBay for a couple of years. I was working for eBay classifieds, which was mostly Gumtree in the UK, as well as some central eBay projects.

I got quite frustrated with being in a big company environment – there were a couple of projects that I worked on that, despite clearly being the right thing for the product, ended up being killed as they were viewed as potentially stepping into competition with the core eBay product.

I moved to GoCardless, and I credit that with being where I learned an awful lot about how to do Product well. I joined at quite an exciting time, where they brought in Carlos Gonzalez-Cadenas as the CPTO, and there was this big surge in investment into product development. I got to be surrounded by a lot of really smart Product people.

Why did you move on to Pelago Health?

Not to sound too cynical, but with all the products I’d worked on, I had this sense that if the product didn’t exist, the world might be a little worse, but not way worse. I’d not had the opportunity to work on a mission that I was really bought into.

So I joined Pelago Health as a founding PM at 12 people, Series A. I did ~3 years there, ending up managing an org of about 50 people, 6 PMs, as VP of Product. They raised $75 million in Series A and B funding, and launched some pretty innovative and interesting products, mostly focused on treating people with alcohol and opioid addictions.

Obviously, it was challenging as well, having to delve deep into topics around trauma.

So it was a good success story?

Yes, and they established themselves as one of the leaders in US Healthtech. And having such a strong mission made it easy to rally people around a cause – it becomes your superpower and fuel for the team.

The flip-side was that a product launch has a totally different meaning when you’re trying to treat people for, say, an opioid addiction. What really is an MVP when you’re dealing with life and death?

We had to have conversations about how we would handle the inevitable situation where someone using our products overdoses, not because of our product, but whilst a member of our product base.

That stuff started to weigh on me pretty heavily and became quite consuming.

Was this what made you move on from Product?

There were some push and pull factors.

From the push side, I was part of the executive leadership team and in that environment, I found it to be pretty draining on my energy and overall wellbeing. I was starting to question whether I could imagine myself doing this for years to come – and the honest answer was probably not.

But also, I think I’m pretty good at Product, and I’ve had a decent career with some interesting stuff. But I don’t love it in the way that I saw others around me loving it. I’m somebody who wants to love what I do and be great at it.

On the pull side, I’ve always been inherently fascinated by people – why they think and behave how they do. And when I looked at my experience as a Product leader, I realised that the bits that I found the most energising and impactful was coaching the team and seeing them succeed.

Finally, on the more personal side, in my early twenties, my parents divorced (amicably). However, my mum ended up in an abusive relationship, on and off, for about three years. Figuring out how to not let that consume me became a catalyst for me – I ended up learning to teach yoga and meditation, and went deep on a lot of different practices.

So that prompted the move into coaching?

Coaching felt like the conjoining of these worlds – the start-up world I’d been living in. And the parallel life in which I’d been teaching yoga, meditation, and the decade of self-discovery I’d been on.

I trained initially as a transformational coach and started working with a few clients. I realised it energises me and plays to my strengths.

Initially, I did this alongside my Product role, and then decided to double down on the coaching. I still do a bit of Product advisory stuff as well, but my focus is on the coaching.

So what does an exec coach do?

It’s not a particularly well understood path, although it’s becoming more so. The same is somewhat true of Product - I guess I pivoted from one poorly defined career path to another!

Based on what a lot of those people are doing, I’d term them advisors or consultants. This sort of relationship is based on an asymmetry of information – people come to you because you know something that they don’t due to your domain expertise.

When I talk about coaching, I mean much more of a peer relationship. Sometimes it can look a bit like therapy, sometimes it’s more tactical than that. It’s really focused on how you empower someone to do their best work, be their best selves, and figure out what’s important to them.

A lot of the time, frankly, it’s about helping people get out of their own way – because many people already know how to navigate these situations. Despite having all the information, we still end up in these cycles of anxiety, imposter syndrome, inaction, languishing etc. A lot of this can have quite deep psychological roots.

To the extent that you can, can you give some examples of the sorts of topics you cover?

On a one-to-one basis, I’m mostly working with founder and leadership-level execs. With that, there are typically three levels of issue you can help with.

1. Situational – for example, a younger founder who finds themselves with hundreds of employees and is coming across lots of situations they haven’t navigated previously. It could also be another exec who has a challenge managing up, or dealing with founders who have very strong wills.
   
   These are often quite quick to resolve. Once you unpack the situation with them, they will often quickly identify what they need to do. They sometimes think, ‘why did I even need this coach?’
   

2. Skills – for example, how can I take this situation and generalise my behaviour into a skill I can apply in similar situations in the future? This is more mid-term.
   

3. Mindset – a good example here is how to deal with imposter syndrome. You’re really here to help them see their blind spots, understand their own thinking, how they process the world, sometimes challenge them to see it from a different point of view.

There’s also just some baseline accountability, too – your client has a situation, has identified the way to navigate it, what they’re going to do next, and just your presence as a coach helps keep them accountable.

And I don’t mean ‘accountable’ in how it’s used in corporate environments (where really there are negative consequences for not doing something). It’s more from a point of curiosity – what was it that stopped you from doing what you said you were going to? How do we get past that?

Do you think Product set you up well for this?

Yes, I think so, in three areas:

1. Skills – if you’ve had experience leading and coaching teams, that helps. Also, when Product is done well, it’s a role that is uniquely strong at first-principles problem-solving.
   

2. Experience – there’s a debate around whether you need to have operator experience to be a good coach in the start-up space. I don’t think there’s a right answer here, but personally I don’t think domain knowledge is critical as a coach. However, my experience means that I have a lot of common frames of reference with my clients – we speak the same language.
   

3. Building a business – your biggest barrier is getting clients and building a business, when you get started. Almost all my clients came directly, or one order removed, from my network.

One thing I’d say – the world of start-ups is hard and I see a lot of people looking at their next step. I wouldn’t undervalue your skills as a Product person – if you’re looking for a change, coaching can be phenomenal, but take the time to work out what it is that energises you and lean into that.

How should people find out more about it?

There are a few governing bodies – the best known is the International Coaching Federation (ICF). They don’t train you directly, but they oversee coaching schools.

I initially went through a coaching school called Animas. That was all done online over the course of about six months and I’ve since gone on to do further trainings.

My advice:

1. Before you explore it, ask yourself – are you really deeply fascinated by people and the intricacies of how people think? Do you get energy from helping them solve these problems? If the answer is not a definitive yes, then this type of coaching is probably not for you.
   

2. If the answer is yes, go and do your research on different coaching schools, speak to coaches, find out where they trained etc.

Can you expand more on why it’s important not to practice without training?

You’re going into a very close relationship with someone.

There are quite clear clinical boundaries that you need to understand. Someone who hasn’t trained, for example, may not spot a scenario in which someone needs further professional help.

More broadly, the nature of the relationship is deep and probably unlike any others you have in your life. My coaching clients talk to me about things they don’t talk to their spouse about. That means you are handling people at their most vulnerable states, and all sorts comes up. If you don’t know how to handle that situation, you’re putting your client and yourself at risk.

Thanks again to Seb for giving us such a thoughtful insight into coaching.

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