Your ability to anticipate maybe undermining your team

To rise to a CTO role, you are probably an experienced technologist and, as a result, great at anticipating events. This may not be the best help you can provide the team. Here's why.

Photo by Darren Lawrence on Unsplash

In the first few years as a CTO, I was frustrated that I could anticipate an eventuality, highlight it to the team and still see the occurrence take place with the team not adjusting in time. For instance, maybe there’s an underinvestment in quality or stability or maybe there’s a stakeholder getting increasingly frustrated and about to escalate.

As a coach, I find many CTOs in a similar position. The scenario is common, the leader is telling the team something is going to happen. Given their experience, they are seeing the signs everywhere, and the team seems oblivious. Or they are aware but seem unable to follow the course correctly.

Being in the position of giving the ‘I told you so’ becomes routine. Nothing changes; the team gets frustrated, and so does the leader.

Sometimes, an even worse pattern eventuates: the team will respond and take action and then seek guidance on the next action and the next. And they don’t ever get to a position where they will make the observation themselves. Rather they have become dependent on the leader to identify potential issues they really should be capable of spotting themselves.

Every time the leader tells the team about an issue they predict, they are not helping the team develop the capability to identify situations for themselves. The intervention is ineffective and establishes that this is the role of the leader.

There are, of course, exceptions. The rule of thumb I used was to assess whether the failure would be ‘safe’ for the team. You would define what ‘safe’ was based on the context of your organisation. For instance, would it put their job role at risk or affect the safety of staff or customers? But as risk-tolerant as you could afford to be, I would prefer to allow the team to fail and learn safely.

The shift I made was that I should see this as my failure rather than the team’s failure. By taking this perspective, it forces you to start asking questions such as:

• What do they need to know to anticipate what I am anticipating?

• Is there adequate experience available in the teams for the relevant subject matter?

• Do you know if the team has the right stakeholder relationships and engagement? Do they know the different parties who may be invested in the outcomes for which they are responsible?

• What incentives may be driving current behaviours?

• What obstacles might they be facing?

In many ways this is an extension of the idea I covered in this post:

A common pattern observed with poor or inexperienced leaders is that they will internalise successes as part of their personal brilliance and externalise failures as the flawed execution of others. Irrational confidence is often a trait that has helped an individual reach a leadership position.

Unfortunately, it’s often a problem organisations’ have enabled, and it’s not always addressed quickly. It’s not uncommon to observe leaders of all levels and variety of success succumb to the same folly.

An ex-colleague once shared with me the hypothesis that it is human nature to seek a situation where they cannot personally fail unconsciously. You could call this chronic motivated reasoning - which, if you are not aware of it, stands to reason as being a behaviour likely to be repeated.

Whatever the cause, I’ve found it good practice as a leader to be clear that you are accountable for your team’s performance. Their failure is your failure, and thus, you need to be constantly looking at what you can improve in terms of:

• The information (context) they have.

• Their capabilities to meet the challenges they will face.

• The training they receive.

• What will they learn on the job?

• What will be a focus for our hiring?

Of all these, the most common yet easily addressable issue is the effort a leader has made to provide relevant context to their team. Leaders underestimate how much information would help their team perform optimally. ‘I told you so’ is empty calories. That effort to communicate something that will lead to an inevitable poor outcome could be better spent proactively communicating what the team needs to anticipate better themselves.

After all,

Do you agree that leaders need to be more accountable for how they support their teams? Is there any learning value in saying ‘I told you so?’. Share your perspectives in the comments.