This is something I personally struggle with as a coach.

Quite often, my default style is to push my clients beyond their comfort zone. In so doing, I run the risk that it becomes MY vision over THEIR vision. Or that I may be pushing them too hard, far beyond their capacity to change.

But at the same time, meeting them entirely where they are strikes me as a wimpy approach. One that will, at best, succeed in their transformation taking many years. But it’s a common philosophy that I hear repeated by many agile coaching firms who seem to be looking more at long-term revenue flow over client adoption acceleration and ongoing success.

So, the question is – what is the right stance or posture when meeting a new client?

Should we meet them where they are and apply very little change pressure (where and when needed)? Or should we take a risk and push them out of their comfort zones?

And of course, the general answer is – it depends and context matters. But still, we need a general strategy. So which way do we lean? Let’s explore the extremes of that question…

Why meet them where they are?

What does “meeting them where they are” look like? To me, it starts with compromise. We as a coach generally understand:

  • The set of tactics it takes to execute agile delivery well;

  • The culture’s where agile thrives and where it does not;

  • The scope of the client’s request (expectations);

  • The results that are possible when agile is “done well”.

But if we think the client isn’t “up to it”, we’ll water things down so it’s less disruptive of a change. These conversations often look like this:

  • We (the coach) begin explaining the aspects and challenges of adopting agile to (leaders, managers, and teams)

  • They (the group we’re speaking to) – push back. We hear things like their domain is too complex, or regulatory concerns, or we simply can’t do that, etc…

  • We (the coaches) then acquiesce.

Quite often the clients leave these conversations feeling quite good. They feel like they can “become Agile” with very little change to their status quo. Imagine that?

And the coaches leave these conversations, at least the responsible ones, feeling quite sad. They entered with a fairly solid recipe for agile transformation. Challenging, but doable if folks recognize their need for change. And they leave with a minimal set of agreements, that might affect a slight improvement over the status quo. But nothing close to the potential of a committed agile transformation.

Now, this approach does have merits:

  1. It eases the client into agility;

  2. It’s a small / incremental change;

  3. It’s low risk, not only to the client but to the coach;

  4. It doesn’t cause too much turbulence in the organization;

  5. It allows everyone to embrace the change at their own pace;

  6. It often allows folks to “opt out” if they wish;

  7. In large enterprises, at scale if you will, it fosters an incremental approach;

  8. It looks more like a Kanban, meet them where they are and respect the existing state of things, approach.

From a coaching perspective, it’s a long-term process, so it keeps coaches on the ground for a long time and it drives revenue.

In general, this approach feels quite good. And it does meet the litmus test of “we’re going agile…”. Now let’s look at the other side of things.

Why NOT meet them where they are?

I saw this quote/post from Tobias Mayer on Linked a while ago. And to be frank, it’s what inspired this article.

"If you meet someone where they are, you'll work with them where they are, and when you leave they'll still be where they are."  I credit that to Ron Jeffries. I have paraphrased, and possibly misinterpreted, but nevertheless I find my memory of his words a useful reminder to invite people to a new place right from the start. Beginning with as little baggage as possible gives the process of co-creation a chance. Movement is more likely to occur if they have already made the effort to get out of their safety zone.

Here's the original context for Ron Jeffries' quote:

Now in the original article by Ron Jeffries, Ron is actually lamenting the fact that we’re not focusing enough on developers and agile software development skills in our transformation efforts. And that’s, unfortunately, also true.

However, the same sentiment and concerns around meeting them where they are apply to all aspects of agile transformation. At least from my perspective.

However, there are risks when you push your clients, for example:

  • You can fail to acknowledge or appreciate their strengths;

  • You can fail to understand or appreciate their historical journey;

  • You can clearly push them too far. For example, push them way beyond what their current culture can support;

  • You can push their leaders too hard – to change, to look in the mirror, to empower their teams, etc.

  • You can take on way too many things at any one time – overloading the organization;

  • Ultimately, you can lose the client.

So clearly pushing far beyond the comfort zone of the client and organization.

Can we do both?

There seems to be a “middle ground” alluded to in the conversation that Tobias inspired. Something in between. But if so, what does that look like?

Acknowledge the Past

First, I think it starts with acknowledging the successes of the past. Creating a reflection point where you and the client re-discover what they did well. They’re strengths. The things that made (and make) them who they are.

Very often clients (and coaches) forget to adequately do this. Take some time at the very beginning of any coaching engagement, to discover the organizations or groups success path. Don’t allow this to contain negative or constructive elements. No, it should be purely positive events and wholly celebratory in nature.


Let’s face it, agile done well is a challenge. It changes all aspects of leaderships role. It places significant challenges on the teams. So, a big part of the challenge step is holding up the mirror to the organization so that they can:

  1. See their weaknesses, mistakes, current position in the market, etc.

  2. And then review how an agile / lean mindset, principles, and tactics can help them compensate and correct those challenges.

There’s an implied honesty step here. I often speak to clients who are in denial about their challenges. It takes a subtle hand to expose these and not alienate them or create overt defensiveness on the part of the client.

But you (they) must face the WHY behind going agile. It becomes part of the vision and part of the motivation they’ll need.


The next step is to create a shared vision of what agile might look like at the client’s organization. What is the compelling WHY driving the change? What are the possibilities? What are the outcomes? What are the possible future states?

A must here is to focus on the art of the possible. So, naysayers are encouraged to pull down their guards for a moment and to optimistically envision the future. (try saying – Yes, and…) Not only the future their customers want and need, but the future for them, the stakeholders and employees.

Appreciative Inquiry is a great way to wrap this effort. The positive and inclusive nature of AI events, can lead towards a powerful envisioning process that creates a shared view of the future. But no matter how you approach it, it must be:

  • Created from across the organization

  • Compelling

  • Honestly address the challenges

  • Often shows a path to get to the end state

  • Aggressive and inspiring, but seemingly doable

Goal-setting is another key element to envisioning. And that involves setting incremental as well as longer-term goals. Again, these aren’t top-down in nature, but instead goals that are mined from the wisdom of the crowd.

Point being – every agile transformation needs to be able to answer the following two questions:

  1. Why are we doing this?

  2. And what does success look like when we’re done?


Dan Mezick, in Open Space Agility, emphasizes the power of invitation when it comes to agile transformation (change, envisioning, planning, execution, etc.). By invitation, he literally means that…

You don’t tell people to attend a meeting about going agile, then describe your goals and vision for that.

Instead you:

  • Invite them to a meeting;

  • Allow them to opt-in, without penalty to those who opt-out;

  • You leverage Open Space as a vehicle for establishing your vision for the future and plans for taking some goal-driven next steps;

  • Then use an iterative model to take steps to achieve your shared goals.

The key here is moving from a deciding-telling posture, to opening it up to invitation-shared ownership model.

Dan’s discovered that the simple act of inviting them in (people, teams, groups, organizations) is the best way to meet them where they are and inspire change from within the group.

Change Management

There’s the quote: People don’t mind change…they just don’t like being changed.

What you’re trying to inspire so far is a recognition inside of everyone within the organization of the need for change. It’s a self-reflective process and it takes time for some to come along.

And still others will never move.

So there needs to be a change management strategy formed and in place to help move the organization forward. In a deliberate and thoughtful way. With patience. But with a firm and persistent tempo that relentlessly moves forward.

The leadership team is at the heart of this effort. And they’re actively coaching their teams (and each other) towards the individual-focused agile mindset changes that are key to each and every agile transformation. It’s not a process, but more a sequence of partnered conversations that continue to keep the organizations goals front and center.

Build Relationships

I brought this topic up at an agile coach’s breakfast to help define and refine my thoughts. In that discussion, the idea of relationship building came up. And I’d never actually considered it as part of meeting them where they are actions, but it is.

Right from the beginning of every coaching engagement, I’m trying to build a relationship with my coaching clients. There are a couple of key things related to that:

  • Earn credibility – this can’t simply be how many agile books you’ve read. You have to earn your credibility by your real-world and varied experience. Then, helping the client to translate these lessons to their own contexts.

  • Earn trust – they have to see your coaching advice work. They have to trust you, because they’re literally and often putting their careers in your hands. You build this with incremental and early successes. That’s why the next step is so important.

  • Always, be empathetic – you should never lose sight of their context. Business context, cultural context, leadership context, personal context, etc. And it’s easy to forget this as you move into a transformation. Point being – empathy isn’t a beginning-thing. It’s an ongoing-thing.

  • Listening – one of the best things you can do is become a great listener. I aspire to be a “trusted sounding board” with every client organization. But to effectively do that, I need to talk less and listen more. And this listening is beyond the words. Often you’ll get incredible value by listening to the tenor and tone from the teams.

Embracing the Notion of Just Enough

One of the things that I don’t often communicate well enough as a coach is the just enough nature of my pushing.

By that I mean, I’m really never trying to push an organization beyond their capabilities. I usually have a next step in mind –

  • A critical, situational step

  • A process MVP

  • An agile tactic that needs to be broadly accepted and acted upon

  • A training class that is a key to a successful next step

And I also think that organizations often bite off too much in their thinking as well.

For example, I can’t tell you how often I enter a large-scale organization, say composed of 100-150 agile (Scrum) teams and they present me with a Gantt chart with an “Agile Complete” milestone within the next 6-months.

Clearly, this is not Just Enough or MVP thinking at its best ;-)

I guess what I’m saying here is that pushing to a stretch but feasible goal is healthy. Stretching beyond all reason, is not.

The sequence I’ve just presented are one-time and ongoing activities to meet your coaching clients where they are. Whether your meeting them where they are and/or pushing them, these steps help their ultimate results.

Wrapping Up

As I worked on this article and thought about both sides, I challenged myself to reevaluate my own approaches.

In essence, asking, was I being too pushy?

And in the end, the answer came back…it depends:

  • It depends if I have the client’s best interest at heart; if I’m truly looking to serve them;

  • It depends if I’m trying to accelerate their agility as quickly as possible and then put myself out of a job;

  • It depends if they’re ready for the change;

  • And it depends if I’ve properly gone through the steps I’ve outlined above.

Point being – YES, you do want to meet them properly where they are. But in the end, you want to PUSH everyone beyond their comfort zones as well!

And you must avoid looking at things solely through the lens of revenue. I’ve shared about this coaching mistake before in this post. If you found value in this discussion, that one compliments it quite well.

But in the end, wow, what a tough balancing act!

Stay agile my friends,


BTW: I want to acknowledge and thank the Raleigh-Durham ALN Group – Agile Coaching Breakfast group from June 2018 for allowing me/us to explore this topic in a group setting. The discussion helped frame and focus my thoughts. Thanks, everyone!


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