Ask Different Questions: Building Your Agile Leadership Skills

By: Lorena Connolly | Jun 12, 2019 |  Agile Transformation,  Article,  Leadership

The Situation

It’s Monday morning. 

You’ve just come off a long weekend of work. You were up all night Saturday deploying the product and then had multiple configuration issues to address on Sunday. Now, it’s Monday and you need to be in the office for an 8 AM meeting to hear what the new Agile Consultants have come up with for your organization. You stagger over to the kitchen thinking there isn’t enough coffee in the world to get you through this presentation.

You’re probably thinking, “They can’t possibly have anything meaningful to present. They don’t know what it’s like here.” 

One of your employees texts you letting you know there seems to be a performance issue with the new release. You wish you could skip over this two-hour presentation, get to your desk, and do some real work.

The consultants launch into their presentation, talking about improving the business by organizing into small cross-functional teams and working in small batch sizes.

What makes them think that will work here? If they really want to improve quality, why don’t they get the Sales people to stop making commitments before the technical team has had a chance to say what is feasible? 

Now, they are going on about empowerment and leaving decisions to the team.

What makes them think that the team is equipped to make those decisions? These are decisions that you normally make! And they want you to change the way you manage, too? After all the literal blood, sweat, and tears of frustration you’ve shed to get the deliveries out on time, all the late nights, weekends, all of a sudden, you’re the problem? 

Suddenly, through this whirlwind of thoughts, your boss’s boss asks you, “You’re critical to this being a success, what do you think?”

You look around and see all the smiling faces and expectant looks. Through a dry throat and clenched jaw, you say, “Sounds great, I will get behind it.” 

Silently, you wonder if it’s time to update your resume.


Sound familiar?

When an organization has made the decision to adopt an agile way of working, they often only acknowledge the impact to teams. However, there is also a significant impact on leaders and middle management. This shift requires them to change the way they have been managing and delivering past success to the organization–often without a seemingly tangible explanation as to why.

As focus is placed on the teams and helping them work in new ways, managers are often overlooked. This is unfortunate, as these people are often influential, well-respected, and valued leaders.

It’s no wonder their initial reaction is one of fear or skepticism. So, as mid-level managers, how do we combat our reactions to change and take advantage of the situation we’re in?


How To Start Building Your Agile Leadership Skills

As you saw in the situation above, the questions this leader asked themselves could only lead that poor soul to one conclusion: “This is bad, I’m the victim, and I’m out.” Even though this leader is experiencing the pain of long cycle times, tough production deployments, and production issues, they remain skeptical and on the defense. This is because human nature leads us to tolerate the pain we know and reject/avoid the pain we don’t know.

Don’t get me wrong. An organization should acknowledge a transitioning leader’s emotions as valid and provide the support, path, and plan for this new leadership style. However, at the same time, the transitioning leader needs to work through these emotions and concerns and accept the support, path, and plan. But, how? 

Change the way you approach the problem.


Ask Different Questions

Much easier said than done, I know. I’ve been there–more than once. However, learning to ask questions that open up new possibilities is key to unlocking leadership potential and successfully building your Agile leadership skills. 

In the situation above, we saw an example of how a leader initially thought about the change of an Agile transformation and the perceived threat to their job. In the table below, I provide some examples of how to re-frame these internal questions in order to take advantage of and benefit from the situation:

What makes them think this will work here?

What company-specific research or assessment was done to come up with this approach?  What methodology was used?  What data backs up their findings?

Why don’t they get the Sales team to stop pre-committing?

How can we provide more accurate information to Sales to help them understand the time needed for similar efforts? How can an Agile environment help us partner more effectively with the Sales team? Why does Sales feel the need to pre-commit? Is there an underlying trust issue with our predictability?

What makes them think that the team is equipped to make those decisions?

How do we plan to equip the team to make these decisions?  How can we handle design decisions? How do I need to prepare/support my team?

Why do I have to change the way I manage?

If I change the way I manage, what will I be losing? What will I be gaining? Is the gain worth the pain? What do I specifically need to change? Who can help me change? Who will keep me honest?  

Do I leave the details to the team?

How can I equip/support the team? What methods can I use to stay sufficiently engaged to coach the team without directing them?

I’m the problem?

What am I not seeing that the executives are seeing? Who can give me open feedback on the business challenges we have? How is my team contributing to those challenges? Have I gotten so used to “the way that we do things” that I’m missing something? Are late nights and weekends really how I want to lead my team? How can I show that is not sustainable? How and who can I work with to set proper expectations?  What do I own here?

How do they come up with this stuff?

What are they seeing that I am not? Have they helped other organizations with similar issues? What were the results? Is there a way out of this pain?

Am I no longer critical to the success of the organization?

In this new way of working, in what new ways am I expected to contribute? Does that interest me? Does it open other opportunities? Am I ready to contribute in that way? If not, who can help me get ready? Is there an opportunity to create a new/additional role for myself?

What do they mean by you focusing on “higher-value” items?  

Are there additional skills, tools, challenges in which I can obtain a level of mastery? Are there higher-value problems I can solve for the organization? How might that help my career/job satisfaction?



The truth is, this change will require you to call on leadership skills you may not have yet–or that you didn’t know you had. You will have to think differently than you have in the past to navigate this very real and challenging situation. Additionally, your team will be watching you very closely to see how you respond and will take their lead from you.

As a leader in your company, you understand the value of being responsive to the business needs, improving business outcomes, and improving the work life of your team. Use these re-framed questions and new Agile Leadership skills to help you work through your concerns and map a path to meet the needs of the business. Once you have your own answers, use this technique to help a struggling team member or colleague work through the transition.


Learn More

Register for our Certified Agile Leadership 1 Workshop to get more in-depth knowledge of the Agile Leadership skills it takes to transform teams and organizations.

Read more about building your Agile Leadership skills in these articles:

Looking for more on the role of middle management in an Agile transformation? Check out these content pieces:

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