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CEO Coaching

cause you don’t know what you don’t know

Kulveer Taggar
5 min readSep 3, 2013

Earlier this year I started receiving CEO coaching. I was surprised by just how much there was to learn about the techniques and skills that go into being an effective CEO.

I believed that in a small startup, management wasn’t a thing. Worse, I didn’t know what I didn’t know.

Most CEO types are probably quite driven and self-starters and don’t think they need any coaching. That’s precisely why I think a coach can make a big impact.

It’s been a few months now, so I’d like to share what I’ve learned through this process.

External accountability

It sounds silly to say it, because a CEO’s job is to be accountable, to your customers, team and investors. But having a one-on-one relationship with a coach creates a different type of accountability.

It’s focused - you are accountable to your commitment to improve.

Whether it involves communication, employee motivation, or meeting certain milestones, it’s a decision you’ve made to become better.

The psychology of having someone check in on you on a weekly basis is really motivating. I may fall behind on a self-generated to-do list, but I rarely, if ever, slip up on a to-do list for the week that my coach has set up.

Surfacing difficult issues

Oftentimes, when I’ve been discussing things I want to improve, just the process of talking it through helps uncover the root of the issue. On the surface, it could be something such as a belief that we’re not optimally allocating resources. In reality, however, it may be a symptom of the differences in the vision for the company amongst the founders.

Whilst you’ll ultimately discover these issues yourself, having regular coaching sessions can you help hone in on these issues quicker - and in startups, speed is critical.

Tapping into a larger pool of experience

My CEO experience consists of one prior startup. Though I’ve read a few books, sought advice from mentors, and devoured many blog posts about running a company, I access a different level of knowledge through my coach, who has previously spoken to multiple CEOs across different industries and company stages. The advice I’m receiving is first-hand and from a pool of experience that otherwise would not have been accessible.

Some of the most valuable advice was about company culture.

An environment where employees grow in confidence and competency requires design and won’t happen by accident. If you want team members to learn new skills, be proactive and take more responsibility, then they have to feel comfortable being able to make mistakes. That involves giving both positive and negative feedback in the right way.

For example, I had set some goals for a team-member which they accomplished quite successfully. Obviously, I made it a point to say “well done” and left it at that. My coach then informed me that there was such a thing as a technique to giving praise, (and it’s not just about being nice), which would accelerate learning and build confidence more effectively.

Her brief guidelines for giving useful, and non-patronizing praise were:

1) attach an emotion (“I was really excited to see… I’m so relieved you…”)

2) give a really specific context (“I was really pleased to see how well you handled that conversation with X”)

3) attach a consequence (“you doing X means I can save time doing Y”, or “that’s going to save us a bunch of money”)

4) thank them (“…so thank you, good job. ….I really appreciated it”)

People innately want to please, and not giving praise when it’s due can be demotivating. Everyone wants to work where they feel valued and there’s a supportive culture.

[Aside: my previous modus operandi was modeled on the legendary former manager of Manchester United, Sir Alex Ferguson, after reading his autobiography. A simple “well done” if a high performer did something well, and a rollicking if not. Apparently, reprimanding folks becomes ineffective after a while. Who knew?]

Another subtle point I wasn’t aware of — sometimes women in the work place just do their tasks without seeking recognition for it (i.e. they just see it as their duty and get on with it), whereas men can be much more vocal about letting everyone know when they’ve finished something. If you’re not aware of this as a CEO, it can end up creating false impressions.

Staying focused on the bigger picture

It’s pretty easy to get sucked into the “urgent but not important” tasks in your day to day routine. A week passes with barely a moment to take pause. With a weekly coaching session, everything is looked at through the lens of the one month, three month and six month goals.

With regular note-taking, it’s then easier to track your progress over time and see how you adapt and respond to changes in circumstances.

For those of us who are hyper self-critical, looking back and actually seeing that you achieved your targets is quite reassuring. And for those things you missed, you’ll find out why and can improve on that.

An outsider’s perspective

Your coach has no vested interest in any outcomes other than you doing better at your job. That’s not always the case when talking to cofounders, investors or anyone else who is a stakeholder in your startup. Since being a CEO is a lonely job, it’s good to have someone looking out for your well-being.

In addition, your coach is not as immersed in your market and your product as you are, and therefore can bring fresh insight or ask questions that you don’t regularly get asked, which is always useful.

Better productivity

I know when I’m being productive and when I’m not. Having someone ask you that directly, and then follow up on why you’re not hitting your maximum, forces you to confront whatever obstacles are in your way.

At one point, it was something as simple as irregular sleeping patterns (I yearn to be nocturnal). Then it was the (age-old) inbox problem, which I fixed by being more aggressive with my filters.

Sometimes, it may be nothing to do with the startup but something in your personal life. And, even in that context, having someone you can talk to is very beneficial.

I’m grateful for the coaching I’ve received, especially as I stumbled into it and was initially skeptical. Feedback from my team has also been positive: I’m more effective, morale is better, and everyone feels more confident in our vision and our ability to execute on it.

NB: For those interested, my coach is Lucy Counter.

Ben Horowitz has a great post about making yourself a CEO. I recommend all budding CEOs read it. It’s an unnatural job, but with a bit of coaching, it can become a little easier.

In athletics, some things like becoming a sprinter can be learned relatively quickly because they take a natural motion and refine it. Others, like boxing, take much longer to master, because they require lots of unnatural motions. For example, when going backwards in boxing, it’s critically important to pick up your back foot first, because if you get hit while walking backwards the natural way—picking up your front foot first—often leads to getting knocked cold. Learning to make this unnatural motion feel natural takes a great deal of practice. If you do what feels most natural as a CEO, then you may also get knocked cold.