How we manage the CEO: CTO Dynamic

Andrew Weaver
February 1, 2024

Inspiration for this article arrived via feedback from one of our CTO mentees, who is grappling with the CEO relationship and what he described as a ‘volcanic chief executive’.

Most Sunday nights he receives an email from the CEO delivering a barrage of expletive-led criticisms of the senior management team.

An extract below [expletives removed for those with a sensitive disposition];

“I’ve not received any board reports and have to spend every Sunday night chasing them up. I am perceived as incompetent by my investors because of you which is not only a disaster for me, but will soon be a disaster for you lot.  Pull your socks up or ____ off”

Not sure which Business School he attended but assume he missed the “personal communications” lecture.

It’s clearly an extreme example but as a technology leader who is (becomes) part of the senior leadership team you will be working with and handling a range of very different characters and often the contrast of personalities is at its sharpest with the Chief Technology Officer vs. Chief Executive Officer dynamic.

Even during the best of times, it can be a delicate relationship to manage, particularly if your CEO is a non-techie.

Check also the “11 Things a CTO Should Never Say to a CEO”

So how is it for you?
How do you (should you) manage the relationship, particularly if it’s becoming confrontational and just receiving basic communication like a board agenda manage to increase your stress and ruin your day?

We put these questions to our own CEO:CTO combination here at CTO Academy, Andrew Weaver and Jason Noble who will admit to being a classic example of two very different characters having to forge a successful working relationship.

We asked them to take a hard look at how they manage this business-critical dynamic;

What’s your history of working together?

Jason: We met briefly through an earlier start-up we were working on. Though we didn’t have much direct contact with that project we did bond over football, and the 80s music and it’s always a good starting point for a successful business relationship, to already have a social one.

Andrew: We decided early that we liked the cut of each other’s gib and when we found ourselves exiting other projects at the same time, we discussed our “new ideas” and what we might like to work on together. Jason had been playing around with the brand name of CTO Academy and so we decided to roll out an initial pilot, as much to make sure we enjoyed working together as to test the market appetite.

Does it help to know someone before going into business together?

JN: It’s definitely a bonus and particularly with a CEO:CTO dynamic where the personalities are often very different. Having got to know each other across a couple of earlier projects we felt confident and comfortable about the strengths, weaknesses and synergies.

AW: Absolutely, though it doesn’t mean you are guaranteed sunlit meadows and company success but finding the right co-founder can be very challenging and you don’t know how you might react together when the heat is on so it’s useful to have some experience of working with them before.

So far, so good though not without some battles around our different styles and vision for growing the company and what processes are required, when to apply the 80/20 rule – often a crucial calculation when deciding how and where to use your limited start-up resources.

Where do you see the biggest differences and how do you manage them?

AW: I’m definitely the one fizzing and energised by a constant stream of new ideas, angles and directions. Not all of them are viable or sensible.  It’s particularly important when an early-stage company is rapidly iterating that you avoid running after too many different ideas. Focus is crucial, not always a strong point of mine.

Where it works particularly well is that Jason brings a necessary calmness and reflection to my decision-making process, often making me think more than twice about a particular direction of travel.

Equally, I’ve helped Jason move outside his comfort zone with this project, whether that’s presenting, communicating etc. He’s got so much great experience and a genuine appetite to help other tech professionals, but presenting has never been a strength. I’ve enjoyed working with him in understanding how we can help and support each other in building out our mutual skill sets to the benefit of the wider project.

JN: Andrew is far better than many CEOs I’ve met where literally, you wake up one morning and everything has changed. But he did have a tendency to start firing off new ideas and suggestions, without letting previous changes settle down. After some initial battles about finding a balance and allowing the business model to emerge, we’ve found a balance that works. 

That said our comfort zones are in very different places and mine was certainly never in front of a camera or speaking to large audiences. I’ve had to force myself to get out there and communicate, in a way that seems irritatingly natural to him but anathema to me.

Easier as co-founders than the ‘CEO as boss’ scenario?

JN: Yes, the dynamic here is about genuine collaboration and value creation plus I’m not really operating in a strict CTO role at the moment as I tend to handle other areas of the business such as coaching. 

We certainly operate as equals and that’s not always the dynamic when working with a CEO. 

Whilst there is no proven or definitive approach to this relationship, sharing the journey helps ameliorate some of the classic tensions of working with the CEO as a boss.

When working as a subordinate you want a leader who is on your side, has sufficient emotional intelligence and empathy to listen and not be driving every decision from the top down. Life is too short to spend your working day walking on eggshells and probably the number one skill of any effective leader – CTO and CEO – is that of empathy. Fail to give good people respect and autonomy and they will leave.

As co-founders, we both have a direct influence on value creation and driving the bottom line which definitely drives greater co-operation and diplomacy.

What do you look for in a CEO, Jas?

Particularly in the early-stage companies I’ve worked with, I’ve seen too many CEOs who flit between the latest great idea, often without giving the earlier one chance to settle. I understand the ‘move-fast-and-break-things’ but there are CEOs out there who adopt the extreme version,

In reality, it’s not an easy job so I look to work with someone who can have the vision and be decisive but is also consistent and capable of holding their hand up and communicating when things might (and often do) go wrong.

A 2017 HBR survey reported that among CEOs who were fired over issues related to decision-making, only one-third lost their jobs because they’d made bad calls; the rest were ousted for being indecisive.

Andrew is rarely indecisive, indeed sometimes he is too proactive and my biggest challenge in the early days was making sure he was effective with his (and our) time management.

Another big issue I’ve suffered from in the past is with defensive CEOs who failed to leave their ego at the door. Often they suffer from a fixed mindset that is protecting themselves rather the benefiting the entire company.

I know from the coaching and mentoring calls that I’ve done that this can be a regular issue, that many of you have been at the behest of CEOs and those in other senior executive roles where the emphasis is about them, too focused on financial performance and metrics that trigger their bonus whilst ignoring other key factors about what makes a business and a working relationship successful.

What do you look for in a CTO, Andrew?

Someone who understands the other side of the CEO role and in particular, understands the intersection between the technology and the business – something we focus on within our leadership courses at CTO Academy.

Ideally, someone who can combine the technical with the practical and doesn’t get stuck in the weeds, particularly during the early days when momentum is everything. A startup CTO in particular needs to learn and become comfortable with the inevitable trade-offs that come with the territory and not someone who hangs on for the perfect solution. Going back to the 80/20 rule, they need to accept it won’t always be absolutely right as long as it’s effective.

I need them to be commercial and agile.
Don’t be building products with all the gizmos, that the market doesn’t want and/or hasn’t validated.

How do you manage remote working together?

AW: We were lucky when Covid arrived that we were already a 100% remote team. I’m in Madrid, Jason is in London and the rest of our team is distributed around the world – Brazil, USA, Argentina, Namibia.

I’m an early morning person and had a bad habit of flooding Jason’s email inbox every morning which could overwhelm his schedule so we slowly developed a more orderly process in terms of our internal reporting and task allocation. We use Nifty to project manage tasks more effectively and regular check-ins that help to prioritise.

We’ve also discovered the power of actually meeting in person so we arrange regular in-person get-togethers which from our experience, can be enormously productive in aligning on strategy and bigger ticket items.

JN: Yes, I often woke up to a ridiculous inbox which as a big process person meant I had to train Andrew early about how to communicate in a way that didn’t overwhelm the rest of the team.

AW: I wasn’t always great with the process, tended to throw ideas out as they emerged and some training was required in particular on how to manage online communications.

But we’ve adapted well. We do our best to manage an efficient process, keep meetings to a minimum and ensure we don’t overwhelm each other or the team, and maintain lots of outside interests and wider quality of life.

And this is an important point in terms of the cultural guard rails that we are building within CTO Academy as our remote team grows around the world.

We share the same perspective around a work/life balance and instil that in our teams with flexibility embedded into how we work and the autonomy that gives others.

Leadership comes from the top and those guard rails are tough to shift once the company gets any kind of momentum so learn how to work well together in the senior leadership team and the principles and values that you want to flow down through the company as it grows and scales.

Have you found the Yin, to each other’s Yang?

AW: I’m not sure who is the Yin or who is the Yang, but so far so good.

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