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Communicating with Senior Executives

Communication & Intent3 min readAugust 2026

Earlier in my career in a galaxy far, far away

We had delivered a project within a fraction of the time that had previously taken another set of teams for less functionality. The reason for this success was:

1. Team: Having a great team of A-players.

2. Commitment: We didn't actually stop working through the weekends.

3. Executive support: I had direct support from the C-suite with daily calls with one of them.

The work was run independently, with my manager and his manager staying away from the project (as it was seen as totally impossible they didn't want anything to do with it).

We delivered, tried to catch our breathes and then suddenly those people who weren't involved wanted a meeting.

"I was speaking with the CEO and marketing about the project we delivered." said the most senior person on the call (the manager of my manager), "They said it's necessary that you deliver to a new set of customers in two weeks.".

"I see, so did you say that we would look at the feasibility of this. Pushing through the functionality so quickly before was a big challenge.", I said.

"No I told them we will do it. This should be trivial now, unless you haven't futured proofed it.", said the senior manager referring (unknowingly to a project that used many shared legacy systems).

"I'm sorry but the amount of time it took previously to properly test that scale of new functionality and have it signed off by Risk and Compliance was more than that. I can take away the requirements to the team and we can estimate how long it will take.", I replied.

Moment of silence from senior manager, how dare this upstart get in the way of making them look good infront of the CEO!

My manager chimes in, thank goodness he's going to support the team that just delivered the impossible for him. "I think what Mike is trying to say is, that we can do it", said my manager.

The reality of communicating with senior executives

When talking with senior executives it is sometimes easy to lose track of the actual realities of the situation.

This is especially the case when you are a high performer that has differentiated yourself by working hard, producing great results and getting on with your job with a dedication and focus that has been praised by your manager. It could be that you think if people work hard then they do well, this perception of meritocracy is very prevalent in people that have had the balance of not being very expensive and producing higher than expected output and being a safe pair of hands.

Now depending on what type of manager you have, this positive feedback may have been passed through to the senior executives (A-player managers promote their teams and their performance determines their value) but it is worth understanding the realities of how the communication is likely to have occurred.

There is a high likelihood that the senior executive has never heard of you, or perhaps has only just heard of you and that they made a note of your name (added to the other thousands of people they will be talking with in the course of the year). If your manager talks about you all the time then they look weak to the executive and also appear a bit redundant. If your manager mentions you at all they are likely to position you as one of their team, who they manage. That you are a good performer and need mentoring. Again this is just the way that your manager will position you without letting go of the fact that they are still very much required.

A meeting with a senior executive is therefore a reset, not a continuation of your relationship with your manager.

1. Know exactly what you want from the meeting

Define the objective: Now, before you talk to the senior executive it is worth prepping for the conversation to make sure that you are not accidentally providing a negative impression.

Understand the purpose: Is the meeting objective clear? Is it that you are providing an update on something difficult which is in progress? Is it that you are requesting funding for something and have to show you can deliver? Is it that you are having to report on something negative such as a poor customer experience, a failed bit of work or a mistake that has had a negative impact?

Keep the message clear: The reason for this preparation is that you need to be clear on your message. Senior executives are constantly dealing with very serious issues, this is part of the job and anything not falling into the serious (think lawyers, compliance, decisions that could cost millions) will be not really be given much attention.

2. How can they help?

Give them a useful role: The other reason for preparation is you need to understand how you want the executive to engage with you. People will generally like to be helpful, they don't want to do too much work and also want to feel good about their position of power, etc. So if you can ask for support, a favour to be asked from a different part of the organisation or similar, that is not actually that difficult but can make the senior executive feel like they helped you then that is ideal.

Avoid unnecessary escalation: You DO NOT want to escalate about other people (this becomes a headache for a senior exec and they will see this as you not being able to manage your problems).

Make the meeting worthwhile: You could not raise anything but then the question may be asked why did you waste the seniors execs time?

3. Do not over-rely on preparation with your manager

A-player managers: Another preparation tactic is, do not over rely on preparation with your manager. If they are an A-player they will be happy for you to input without guard rails (trusting your judgement or pushing back where they disagree).

Conflicting narratives: If they are not, then they are met with a challenge in this situation. They have communicated one version of the truth to the senior executive, they will be unable to reconcile what they have said e.g. you're a high performer however you still need "mentoring", this results in the situation where they will generally step in to undermine you to validate their previously communicated messages.

Prepare to stand alone: As a result it is essential that you prepare your input so that it can stand alone. Imagine your manager is not there.

4. Make sure your value is visible

Do not undermine your manager: Now, this does not mean undermine your manager however, you need to ensure that you are seen for the value you can provide and are not caught in a trap of propagating any negative information that has been fed to the executive beforehand.

Protect your future position: This is especially important if your manager moves to another job.

Manage the executive's perception: If you do not manage your communication effectively to the senior exec you will have the legacy of being seen as a junior resource (who did need mentoring) and therefore not viewed as a high performer, and NOT a potential replacement of your manager.

Communicating with Senior Executives
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