The CTO Playbook

Chapter One - The CTO Blindspot

Picture the scene: You're attending the weekly executive status meeting. All the senior executives are there, including your boss. The meeting is running smoothly until - without warning - the Head of Marketing dumps the recent project failure squarely in your lap. Everybody in the room turns to look at you.

Ok let's wind back a little....

For the purposes of this exercise, imagine you're starting in a new role as CTO of a small-medium company that makes, say, taxation software for small businesses.

In your very first days you start by scheduling meetings with your team, to introduce yourself and kick off the process of getting to know them.

Being new to the role and the business, there's an enormous amount of information to take in. It's virtually impossible to absorb it all, or even to know what's important at this point.

But you knew going in that this would be the case, so as a temporary measure, you ask each of your staff to present the biggest problem they're facing right now, offering to help if you can. This allows you to quickly identify what may be critical issues, and gives you insight into how people present and manage problems.

That done, you start looking at the tech stack, the system architecture, infrastructure, vendors, security, compliance and regulatory requirements and risk management. You also want to understand the customer, review the product roadmap, and get to grips with the delivery capability of the teams in your departments. HR is asking to sign off on a bunch role changes, and the accounts team are asking for sign-off on various vendor invoices.

Your calendar fills up depressingly quickly. Some of this is tactical and some (such as getting familiar with the tech stack) is needed to build any longer-term strategic goals.

(Perhaps we'll do a future chapter on how and what to prioritise when starting a new CTO role?)

As you work through this, you start to build a picture of what you're working with, where the gaps are, and what will be required to take the department to the next level.

So far so great.

But now you're in that executive meeting mentioned above, and everybody's looking at you.

It's not a comfortable position to be in. In this scenario, you haven't been in the business for long, so you may get a little grace period, but that won't last for long.... but one thing's for sure: technology problems are guaranteed to happen again.

But do we need to have the subsequent executive 'please explain' moments? How do you prevent this? This is important because whenever anybody in the organisation says "we can't deliver because of technology" - that's YOU, and it's a reflection on YOU.

It's always your responsibility, and it's always your fault. (There may be edge cases, but I'd strongly recommend against acting like your situation is an edge case!).

But don't read that as a negative thing - that's actually your opportunity.

You prevent this by understanding and addressing the CTO Blindspot that I named this chapter for - so let's get to that.

The CTO Blindspot

The activity missing from the above scenario relates to your peers - the other executives and CxOs around the business who are responsible for running the rest of the organisation.

And you haven't spent enough time understanding them, what they need, what their frustrations are, what their constraints are, or why they seem either cynical - or in the worst cases - hostile towards the technology function that you now own.

Building a productive and professional relationship with your peers is a critical part of your responsibility. And that's what many new CTOs miss. The health and success of the business depends on this, and it's essential to your success as a CTO.

Having those relationships in place means you're much more connected and familiar with what's happening in the organisation, and it means that in these cases, your peers have already raised their concerns with you and you've already addressed it.

It shouldn't even make it to the executive meeting.

On those occasions where something is consequential enough to be raised, you should be bringing it to the meeting in partnership with the other executive, and as part of that process you've already aligned on next steps and solution.

If you're ever surprised by something raised in an executive meeting, it means you're not doing this effectively.

This blindspot is more common to first-time executives, as success at lower levels of the organisation relys less on building and managing these relationships.

So to wrap up....

Your primary responsibilities as an executive are 'results & relationships' (which is a progression from 'results & retention' being the primary responsibilities of managers - shout out to Manager Tools for this insight).

The relationships you build with your peers - and by extension the rest of the business - are critical to

1) understanding the needs, frustrations and dependencies of the rest of the business

2) understanding that there are problems that must be addressed

3) helping to get them addressed with as little friction as possible and

4) ultimately delivering results

...and results are what you're actually paid for.

Conversely, if you neglect in developing these relationships - or worse, allow or contribute to negative relationships at the top levels of an organisation, don't assume it just stops with you. Your direct reports will sense it. They will pick up on inconsequential signs of disrespect and it will filter out in their behaviour and down through their team. And again you are responsible for that - for all of it.

This will cause friction between departments, it will result in less effective communication, and in particularly bad cases it will result in omissions or tardiness in process or communication that can amount to project sabotage. Obviously this is damaging to the business as much as it is to your results and ultimately your career.

In future posts perhaps I'll talk about some more concrete steps to take in order to build these relationships, enabling your department to be transparent to the organisation and how to communicate and internally market what your department does to the rest of the business.

Link to Chapter 2: https://www.dhirubhai.net/pulse/cto-playbook-rob-hill-wwp1c