How to (agile) coach executives—nine things to NOT do

Getting time in front of executives is a key opportunity to influence an enterprise; here's how to ensure you avoid some common pitfalls.

This post does not reflect any specific executive team but is more a collection of my insights from across my career; both as a leadership coach as well as an agile coach working with executive teams. Below is my list of don’t dos when working to influence executive behaviour.

1. Don’t make them feel stupid

New agile language can be confusing. To introduce new language when you first meet an executive team is a sure-fire way of encountering the “eye roll” a sign of dis-engagement. Executives deal with important issues that often need timely decision making to resolve and impact 1,000s or 10,000s of people and or community/society.

So unless you’ve been invited in to teach some new concepts and associated language; don’t confuse executives and make them feel stupid (reduce their mastery).

2. Don’t coach or facilitate without permission

Coaching without permission is to impose your competencies on people without them asking; ambush coaching. So if you are in front of the executive do not assume you have a license to coach or facilitate. Executives are used to having information presented to them or a decision put to them. So if you have not been invited in to facilitate or coach then don’t.


Failing to obtain permission to coach or facilitate will only lead to resistance and increase the chances of your not being asked back in to work with the executive team.

3. Understand you are going into their tribe and onto their turf

Going into an executive team means you are entering into their tribe, their space, their processes and agreed norms. So, although you may want to resist whatever processes, PowerPoint pack templates or what may seem like over-engineered preparation, what you need to appreciate is that this is their current state of affairs. Unless you have permission to disrupt this as-is then don’t.

4. Don’t assume they are a team

Executive teams may not have high levels of team maturity. Often executives have strong personalities and are valued because of this. So the collection of executives may or may not have high levels of inter-personal connection and rapport. Don’t assume your ideas will be received in a consistent manner. You may even expose large differences of opinion that leads to open conflict. So just be careful; you do not know what you are walking into when you first work with an executive team.


5. Don’t overdo content; get to the point

Nothing annoys intelligent people more than folks that do not value their time and appreciate their ability to understand complexity quickly. If you are invited in to talk with an executive team get yourself and your ideas organised so that you have a focused conversation on the things that you need discussed. When you get your time use it wisely, get to the point and have back-up material ready to deepen the conversation as required. Get this wrong and you'll notice mobile phones being more interesting then you are.

6. Don’t attempt to move them along the journey too far all in one session

Change and coaching often takes multiple conversations; so don’t over-coach or attempt to over-influence all in one encounter with an executive team. Overloading executives with too many new concepts too quickly will just lead to resistance and dis-engagement. So choose the point you want to make and relentlessly focus on it in how you present your information/ideas. If you have more than one priority going in then you have no priority. 7. Principles are better than practices and agile language

Use normal person language and advise, teach, coach or facilitate from principles as opposed to agile language or practices with strange names. Talk using concepts that are mainstream in business; cycle time, value, delivery, engagement are all good but avoid terms like social contract, ceremony, cadence, sprint etc.

Too much new language will get their eyes rolling and lead to dis-engagement.

8. It is NOT important to be right

Some of my more epic failures with executives were when I felt I needed to make a point; in other words; be right. So let me be clear

“being invited back is more important than being right”

9. Ensure you get invited back

Novice agile coaches often ask me what they should do to prepare to meet an executive for the first time. Anyone who has spoken to me about this knows my answer on what the outcome of your first executive meeting should always be.

“To be invited back for a second meeting”.

Coaching is about having an open door to do your work; to have influence/impact. Closed doors do not let you do your job.

Final words

You are probably seeing a theme here. Doing enough to get what you came for without disrespecting the executive’s world. Lose your attitude, go in humble, curious and respectful of their role and you will improve your chances of being invited back to continue supporting them in their agile journey.


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