3 Agile Strategies to Deal with Difficult Management

Dec 4, 2019

As a member of an Agile Team, have you ever had one of the following complaints about management?

  • Their deadlines are too tight.
  • Their expectations are unfair because they don’t follow Agile processes.
  • They don’t take time to learn more about the work that’s being done.

It’s true, management can be a pain sometimes…so what have you done about it?

Often, there is little to no pushback from the ones doing the work. You and your team expect leadership to actually lead the change, and often this becomes a justification for inaction or paralysis. While it’s important for leadership to step up, it’s also only half the story.

Instead of waiting around for management, consider taking personal responsibility. Sure, it’s easier to go along and blame others for what you perceive as unfairness. However, if you are brave enough to be self-directed and speak your mind, then you will ultimately be more accountable, engaged, and happier in your work. Furthermore, most people welcome respectful, but assertive behavior. So if you’re on an agile team, feel blocked, and aren’t sure what to do, this article offers three strategies that have led me to success. I hope they work for you, too!


1. Practice Empathy

Practice Empathy

Whether you choose to remain quiet or assert yourself, empathizing with others can be an incredibly powerful tool. Try walking in the shoes of those you think of as unfairly demanding. When you have empathy, you can better understand what a person is feeling and why their actions make sense.

Having trouble mastering the empathy thing for your boss? Think about it like this: he or she likely feels a lot of responsibility, and fear of failure often inhibits a more agile, adaptive frame of mind. Agile requires handing power over to the ones doing the work, to allow them to experiment and have a voice. For most people, this lack of control is scary and can lead to feelings of uncertainty and incompetence.

If you want to have a productive conversation, keep your boss’s vulnerability in mind. In general, people just want to be listened to, so start your end of the conversation by validating his or her logic: “I get it—you think we should have this done by next week, which makes sense, because the goal is to get the product to market quickly.”

By clearly validating his or her opinion, your boss will immediately feel heard, accepted, and favorable toward you. Then it’s time to establish your own experience and perspective: “However, last time we ratcheted the teams and worked mucho hours, the results were less than stellar and customers suffered. Moreover, several customers told us they’d rather wait a little longer to get a predictable, quality product rather than something unreliable. I think the key could be good customer communication instead of early delivery. What do you think? Can we try baking this into this next effort?”

From my coaching experience, I’ve learned that most leaders and teams want the same things: to solve challenges and create positive outcomes. Most leaders are very interested in making people more productive and happier in their work. In order to move from an adversarial “management vs. us” paradigm to a solution-oriented, collaborative one, both you and management need to actively try. Empathy is essential; it helps everyone recognize they’re on the same team, working towards the same goal.


2. Learn to Say No without Saying “No”

Early in my software engineering career, I was working on a complex piece of military weapons guidance code. My boss (an intelligent man) came to me and said, “Rodger, hot item; can you and your team quickly huddle and converge on X?”

Instead of immediately taking this on, I first told my boss, “Sure, be glad to do that. However, this other important thing we’re working on will temporarily be put on the back burner so we can work on X. Is that OK? Because we’ll work on whatever you tell me is your highest priority.

His response was illuminating and an example for the rest of my career. He didn’t huff and puff. Instead, he said, “No, you’re right; the other item is the higher priority. I’ll let my boss know what’s what.

So how do you stop yourself from being a passive, resentful “order taker” and learn to say “no” without saying no? Give your boss context and information. Provide options and ask for help prioritizing. The other, more subtle, dynamic in play is mutual trust (but more on that later).

Be courageous and take risks. Maybe you’re in a situation where you work for a lesser person who says insane stuff like, “I don’t care how you do it, just get it done.” That can be really hard, but I suggest that you at least try adding your own relevant information to the conversation in a respectful way.

Learn to Say No without Saying "No"

In management science, there is a concept referred to as “conditioning your audience,” meaning that people tend to behave to the level of your expectations. As you send subtle, subconscious messages, your audience can become “trained” in a certain behavior. For example, if you treat someone like a child, then this person will likely begin acting like one. Without respectful but assertive dialog, you wind up “training” your leadership to walk all over you. They will keep asking you to do things, because you tend to say “Yes.” The better option is to engage and provide context. The results will surprise you.


3. Practice Trust and Live the Agile Mindset

Practice Trust and Live the Agile Mindset

As I mentioned before, you cannot always wait for leadership to make the first move. An organization cannot fundamentally transform unless you, yourself, also put in the hard work. To compete and succeed in a globally networked world, you have to be able to quickly respond, change, pivot and execute. If you don’t change yourself, then you cannot expect to play in the agile sandbox.

People will only trust you if you show trust in them. Your leadership is the same. I understand this is difficult. Our current Western culture is built around a 150-year-old industrial management paradigm—top-down, “command and control,” built on distrust. Distrust is inefficient. When you don’t trust someone, you begin setting up mechanisms and feedback loops to verify and “control” outcomes. When you can’t trust, you always feel you have to go back and check. This is exhausting.

To this end, agile ceremonies are important. They’re the tools that teach you how “to be” Agile and how to trust. When you learn something entirely new, you first have to learn the basics. When you fail, you try again, over and over. It’s a mechanical process. You’re taught fundamentals and then—after much repetition and practice—you begin internalizing instinctive behaviors and muscle memory. What initially is rote and mechanical becomes instinctive and second nature. When you persist, you will soon turn into a nimble, agile, fire-breathing dragon-slayer.

You too must do the hard work and change your mindset. Can you begin to trust more and distrust less? Are you willing to trust, possibly fail and trust again? Can you constructively engage when you feel someone broke your trust? “I trusted you and I feel you disappointed me. Let’s start over. We work much better together when our relationship is built on trust.”



Although leadership has extraordinary power to impact an Agile Transformation, you also have an important part to play. Your boss is interested in making your team more productive and happy, so act assertively and stand up for what you believe is the right way forward. Remember, if you treat your boss like an unsupportive yahoo, then he or she will likely be an unsupportive yahoo!


I’ve been in organizations that do the Lean-Agile thing well, and it’s awesome. The focus is on getting stuff done, but also having some fun. Another lesson learned; be patient and nice to yourself, because all this goodness doesn’t happen overnight. How long it takes depends on the hard work of everyone, both you and your leadership.

Through coaching and training, ICON is experienced in helping both leadership and teams embody the Agile mindset.

Written by Rodger Koopman


With over 30 years in technology, Rodger started his career as an Air Force officer developing weapons guidance systems and global terrestrial & satellite networks, working strategically in counter-terrorism at the joint DoD level. After retiring from the Air Force, Rodger was an early employee in two successful start-ups and a key participant in five mergers & acquisitions. When Itron acquired Rodger’s first startup, he was tasked by Itron’s CEO to move to Raleigh, NC to lead and re-organize Itron’s R&D office. Rodger has led numerous successful implementations of highly effective Agile practices and automated DevOps pipelines in both startups and multiple Fortune 100 companies. Now an Enterprise Coach, Rodger is a certified SAFe 4.6 Program & DevOps Consultant (SPC, SPD) and certified AgilityHealth Facilitator.