Coaching helps you create different, better, decisions

Breaking down the reasons why coaching leads to better decisions, and a calmer mind.

Written from an autumnal looking Peak District 🍂

Coaching is a big part of my life these days. I coach people, I receive coaching myself, I’ve invested time in growing a community of other coaches. It’s been a fairly quick transition, from full time product leader to coaching being a core part of how I spend my time. I often make big choices like this from a place of intuition rather than logically writing down the reasons for and against.

But over time, a list of reasons has become clear. This list articulates why I get so excited about coaching and continue to invest in it - both as a career and for myself. 

If you’re thinking about exploring coaching, this will shine a light on why it’s powerful and what to expect. And if you’re already doing coaching, I believe this will help you to get the most out of your coaching. 

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Quick note: the examples I share throughout are specific to product leaders, because that’s who I have the most experience coaching, and that’s my background. But the benefits of coaching mentioned apply across all leadership roles.

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You can be honest with yourself

Communication is hard in startups. As a leader, you have to communicate to many people and be thoughtful about how you show up in all these conversations. 

• “How do I explain the new direction to my manager, in a way that will get their buy in?” 

• “How do I set expectations with that new hire who seems to be off to a slower start than I’d hoped?” 

• “How can I share feedback with my high flying team member who annoyed stakeholders by not looping them into a new strategy?” 

• “How do I motivate a team member that seems distracted in our 1:1s?” 

A coaching space is somewhere you can share what is truly on your mind, in an unfiltered and uninterrupted way (which you rarely get as head of product). You can share things like:

• “I feel unsure about whether this is the right strategy. How do I get buy-in when I’m not sure?”

• “I thought that the new hire was going to hit the ground running and work well with the team, but they don’t seem to be doing anything. Why aren’t they being more proactive?”

• “I’m feeling frustrated at my direct report. I’ve got all this extra work now that people are annoyed by them. I don’t have time to give thoughtful feedback to them, I just want it to be sorted.” 

• “My direct report probably needs a holiday, but I’m not sure whether I can do without them.”

Sharing the real truth is liberating and terrifying at the same time. You’re meant to have conviction and confidence in that strategy. You’ve been practising how to “speak with authority” and now you have a space where you can let that all drop. Talk about how things are actually going. 

If you don’t have a space to share how things are actually going and what is actually on your mind, chances are you have these worries flying around your head at 2am, and that’s rarely productive for any of us.

A good coach will help you slow down and process those thoughts. They’ll know that helping you to articulate where you are today is the first step in making positive change and moving forward.

You understand where you’re limiting yourself 

I find this part of coaching painful at times. You realise that you make big jumps in reasoning and put a lot of faith in untested assumptions. I’ve learnt that product people (myself included) put a lot more rigour into our product thought process than our own personal thought process. 

Take that thought above.

“I thought that the new hire was going to hit the ground running and work well with the team, but they don’t seem to be doing anything. Why aren’t they being more proactive? I don’t think they’re the right fit for this job”

A good coach doesn’t agree with you that this person isn’t right for the job. They will help you break down this line of reasoning to show jumps in reasoning and assumptions you’ve made. They might ask questions like: 

• What were your expectations of this person?

• What have you tried to help that person reach those expectations? 

• What evidence do you have that they’re not right for the job?

Coaching helps you realise - painfully - where you’re making assumptions that have a good chance of being untrue. We make these because it’s often quicker to get to a simple conclusion “they’re not the right fit” than the more nuanced answer “maybe I’ve not set them up for success”.  

Highlighting assumptions means you can then test - yes, test - assumptions and be proven wrong. So following the example, you can share clearer expectations with the new hire and see what happens. Maybe that new hire is super motivated; they just didn’t understand expectations and focus. 

Some leaps and assumptions I’ve made, that coaching has highlighted:

• Me: “I’m not ready to take on the CPO role.” My coach: “What would it look like to be ready?” → I realised I had no good answer to that, and maybe I’d never feel ready. I took the role by the way.

• Me: “I have to make a decision between salary and work-life balance.” My coach: “Talk me through that reasoning” → I realised I’d made a huge assumption that I hadn’t bothered to test or explore. I’ve since learnt that assumption wasn’t true.

• Me: “It’s going to be too hard to get interest in a first cohort of LEAD because we don’t have testimonials.” My coach: “How can you show the value of the programme without testimonials?” → I’d been assuming that testimonials were the only way to show value. We found other ways to show value and had an amazing first cohort.

Having someone point out the gaps in my reasoning lead to a different, better, decision.

You get more creative 

We all know that we need to be creative to be a great product person. But when was the last time you slowed down and gave yourself space to be creative? Creativity needs you to access your imagination, and it’s hard to use your imagination when you’ve got the calendar of a product leader. I’m sure you’re used to the slack messages saying things like: “Can we book interviews over your focus time on Friday?” 

Coaching commits you to slowing down the pace and focusing deeply on one topic at a time. There are silences. You’re encouraged to keep thinking. You’re encouraged to explore options without judgement. You get to put execution risk to one side for a moment, and think about what you really want to work towards - for your company, for your product and for your career. 

One of the hardest challenges to solve for a product leader in an early stage startup is getting to product market fit. Getting to product market fit is a deeply creative journey. Yes - you need to do a tonne of research, but you need to move forward with a unique vision for the product. It’s easy to dismiss ideas quickly when you work on your own, to only extend your thinking so far, to not keep accountable to your focus time.

Working with a coach makes creativity feel energising and fun. Someone helps bring your ideas to life, they encourage you and highlight your strengths. They’re the positive voice that speaks louder than the existential, scared voice that worries you have no idea what you’re doing.

Coaching helps you move beyond books & podcasts 

In a product role, learning from others is exceptionally valuable and important. I always recommend reading the books, listening to the podcasts, and building your product knowledge alongside coaching. You don’t want to reinvent the wheel when figuring out how to run stand-ups, or structure strategy or measure product market fit. 

But as you grow into a product leadership role, it’s not all about how good your product knowledge and craft is. There’s a bigger emphasis on decision making and your own personal leadership. You can read all the books you want, but you need to get clear on how you make decisions, how you lead your team and how you want to move forward in your career. That’s where coaching comes in. 

Coaching improves your decision making

Having to explain your reasoning to someone else creates a higher bar for decision making.

This only works when you trust your coach and build a connection with them.

My biggest piece of advice is: take the time to find a coach that you trust and have a rapport with.

You need to be able to speak honestly and openly to your coach, you need them to support you in creativity, and challenge your thought processes. You want someone that celebrates your success along the way.

Good luck on your coaching journey! ✨