New Boss Hates Agile? Survival strategies for You and the Agile Transformation

The agile transformation is going fantastic, and then — there is a leadership change. An all too familiar scenario is many organisations. The new dispensation aims to do things differently. Well, they were brought in for a reason, weren’t they? So how can they not challenge the status quo — which is fair, of course. The challenge happens when the new leadership’s ideas about agile are pretty different from yours.

It may not always be the new boss, though. Agile transformations in large complex organisations require us to engage with several stakeholders. Not all of them will be the encouraging types, and there will be some tough ones. A few could be even in the “nasty” range.

Recently, I listened to — Handling a Difficult Stakeholder, with Nick Timiraos on the Coaching for Leaders — Leadership podcast by Dave Stachowiak. There was an interesting conversation with Nick Timiraos, author of the book — Trillion Dollar Triage: How Jay Powell and the Fed Battled a President and a Pandemic — and Prevented Economic Disaster.

Trillion Dollar Triage: How Jay Powell and the Fed Battled a President and a Pandemic — -and Prevented Economic Disaster eBook : Timiraos, Nick: Kindle Store

There are some fantastic lessons to learn from this podcast for everyone — especially leaders and coaches who are driving large disruptive transformations and are very likely to face such difficult stakeholders (OK. maybe not as difficult as Mr Trump :) )

I would encourage you to listen to the excellent podcast, and I am hoping to read the book soon. The lessons are so appealing that I had to pen this down in the context of agile transformations. I have had the (mis) fortune of being through a few such leadership changes and not so few challenging stakeholders. While I did survive, the insights would have been helpful if I could travel back in time and live those moments again.

Based on the insights shared by Nick Timiraos, the lessons for agile transformation leaders fall broadly into two categories:

  1. Building a set of “core skills” that prepare you for facing difficult stakeholders (You have to do this before, not when things hits the fan)
  2. “Rules of engagement” to be followed with the difficult stakeholders (This is for when things hit the fan :) )


Core Skill 1 — Increase your Emotional Intelligence

Emotional intelligence is the ability to monitor one’s own and other people’s emotions, discriminate between different emotions, label them appropriately, and use emotional information to guide thinking and behaviour.

This one is a no-brainer as EQ is critical now for any leadership role, given the complex nature of stakeholder management. While there are several techniques to improve EQ, one that I have personally found useful and practised is the “5 second rule”. When a difficult stakeholder gets “on the nerves” and there is a surge of passion to “react”, waiting for those crucial 5 seconds, taking a deep breath improves the effectiveness of that response. Those 5 seconds help you to “respond”, not “react”. There is a lot more to developing emotional intelligence.

There is some excellent advice here and here. Hope it helps.

Core Skill 2 — Build a strong team around you and Invest in the network

Build a strong team that aligns with your thinking when you have the opportunity. Building an aligned team does not mean that you create a group of “yes” men (or women). It would be best to have independent thinking and intelligent people who would stick with you to face the challenge together.

Another critical thing is to invest in building the network across the organisation at all levels and a brand that you are someone who will do what is right for the organisation.

The centre for creative leadership staff sums it up nicely in their article — The top 6 rules of leadership networking.

Leadership networking is about developing and using your networks in a way that builds relationships and strengthens alliances in service of your organisation’s work and goals. The ability to influence others in informal ways rather than solely exercising your positional/hierarchical power is very important in today’s workplace.

Build those alliances well ahead of when you need them.

Core Skill 3 — Playing the Long game

Trump went after Powell on several occasions with direct assaults. Yet Powell was playing the long game. To quote from the book,

Powell had no interest in engaging in a tough-guy showdown with Trump. His overriding goal was to make sure the US economic expansion — which by July 2019 would be the longest on record — did not end on his watch. But a second, equally critical personal mission was coming into view: make sure the Fed as an institution survives the Trump years intact.

Leaders can wipe off years of transformation success by abrupt changes in approach and strategy. While we may not have the same “independence” Fed had from Trump and be able to resist everything, playing the long game like Powell can be helpful. Efforts to highlight the impact of the changes on business drivers are often beneficial.

I once was part of a group rolling out Kanban pretty successfully. A new leadership (a strong well-intentioned one) decided to abandon Kanban and do a significant strategy change towards implementing SAFe (which was picking up at that time. It was a few years ago). While we could keep on arguing that there is no need for change in strategy and approach, focusing on the long term goal of improving the organisation’s effectiveness was helpful. While the implementation label changed from “Kanban” to “SAFe”, we still did a lot of Kanban practices that helped us drive good business results. This approach from our side to the leadership was crucial. You have to play the long game — for the organisation’s success.

Core Skill 4 — Communicate to connect (in plain language)

We all live in bubbles that put strong bias on how we think, express and especially the language we use. The podcast highlights Powell’s ability to use simple, clear language that helps to relate to the general population and not always be caught up in jargon.

I often ask, “Why Agile?” in interviews with Agile coaches. Many of them go into complex jargon about how organisations need business agility or how agile can help us improve the flow and deliver business value faster through the value stream, or something similar. The agile manifesto puts this much more effectively in plain and straightforward language.

We are uncovering better ways of developing software by doing it and helping others do it.

As Da Vinci said, “Simplicity is the ultimate sophistication”. Developing the ability to communicate effectively in plain language to reach your audience is essential.


Once you have developed the skills, the rules of engagement are golden words to live by in working with challenging stakeholders.

RULE 1 — Don’t talk about them

You do not want to ignore them, but you don’t want to be someone who is a bad-mouth either — applicable both in public and private.

RULE 2 — When provoked, don’t return fire

I was once in a meeting with a stakeholder who insisted he has been doing agile for years. “Why the f#$k do we need a transformation program? The agile manifesto is enough, and it is obvious and clearly stated. People just need to follow it.”, was his standard response in all discussions. He was also undermining the work done by the agile transformation team, often in not so discreet manner.

While it is tempting to react, especially when emotions are flared up, it is wiser and practical not to get caught up in this heated exchange — even with explicit provocations.

RULE 3 — Stick to the goal (transformation), not the politics)

It is tempting to play the political game especially when you have built the network, but remember; it helps no one. Skill number 3 — playing the long game and focusing on the organisation’s goals is more important. Of course, as I often advise in my mentoring sessions to younger colleagues, don’t play politics, but don’t be so naive that you are a victim of politics either. Rule number 4 will help you stay safe from being the victim.

RULE 4 — Work with your allies (while remembering rule number 3)

Last but not least, work with the partners you developed to survive and stay sane. Don’t forget rule number 3. No dirty politics. The allies will help you not be the victim, don’t use them to play games.

The Wrap

The four core skills and the four rules of engagement are great wisdom to manage difficult stakeholders — whether the new boss or that nasty stakeholder with ulterior motives that conflict with the transformation goals. These strategies can help survival — yours and the agile transformation program as well !!

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You might also want to read my book “Perspectives on Agility”, available on Amazon in print as well in Kindle format. Kindle Unlimited users read it for free. You might enjoy a quick summary of the book before you buy.

For users from India, you can order a copy from Amazon India or Flipkart



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