Actively Coaching Organizational Leadership

Actively Coaching Organizational Leadership

You are currently viewing Actively Coaching Organizational Leadership

In a previous post, I tried to create a “Call to Arms” for Scrum Coaches and Trainers to do much more than simple, team-based training. While that seems to be a great deal of our focus, I don’t think it’s creating the environment and landscape for agile methods and Scrum in particular to “Transform the world of work”.

In early May 2014, I was at the Scrum Gathering in New Orleans and hanging out with a significant part of the CST and CSC community. A great deal of the discussion on how to “Transform the world of work” is focused on training and certifications. To be honest, I’m quite disappointed on the lip service that is largely given to the world of agile coaching. And coaching “downward”, toward the team, is most of that coaching focus.

I thought it would be useful to explore some ideas around where to focus when we’re coaching leaders within organizations—more of an “upward” focus. I know many coaches are intimidated by looking in that direction. One reason is the greater risk because these folks usually “pay the bills”. But if we’re focusing on true organizational transformation, then leadership should be getting a solid measure of our attention. Here are a few ideas around where to focus that attention…

Leadership Chops

I’ve found that my senior leadership experience across various organizations helps me immensely in my leadership coaching. It gives me examples to share and stories to tell. It also aligns me with the leadership team, so that I have some empathy with their challenges. And finally, it gives me credibility and balance.

In a perfect world, I believe our CST and CSC community should have had organizational technical leadership roles as part of their background. It certainly would broaden our perspectives, as we would at some point in our careers been a part of a senior leadership team delivering software with real world constraints.  It’s not clear to me whether enough of us have that background. My suspicion is less than 20% of us do.

Stop Referencing Dilbert

Really? Yes! We need to be much more respectful of the management community at large by stopping our tendency to stereotype, marginalize and sometimes demonize them. Often we use the term Command-and-Control to typecast management and Self-Directed to encapsulate the agile team models. We speak about traditional management styles having no place within agile teams; yet, we don’t speak about how to be more transformative in moving leaders forward. And then we’re shocked when leaders sometimes react poorly within agile adoption instances.


Another early focus ought to be towards understanding the leaders world—amplifying that quote about “seeking first to understand”. And then, once we gain that understanding, seeking to be more empathetic and taking “their side” first. I’ve seen an awful pattern in agile coaching where we listen and try empathy for a few minutes. But once we hear something we don’t like, we trivialize the effort it will take to move towards a posture or reaction that we feel is “more agile”. That’s not empathy. It’s trivialization and entrapment. We need to be more patient and understanding that leaders have complex backgrounds, experiences and live in complex cultures. Our simple agile diatribes don’t always work upon first glance in these instances.

5-Dysfunctions of a Team

I’ve found that bringing in popular models can truly help transform the organizational landscape. Some of these include:

  • 5 Dysfunctions;
  • Crucial Conversations;
  • Emotional Intelligence;
  • Employee Engagement;
  • Open Space;
  • Systems Thinking;
  • Appreciative Inquiry; and many others

And as part of introducing these within organizations, I usually recommend that leadership engage their Human Resources departments and any Organizational Development (OD) staff in helping rollout these initiatives across the broader organization. Not only do they help improve the organizational landscape, they also augment agile adoption incredibly well.


I’ve found many coaches, myself included, that blame all of an organizations ills on their leadership. If anything comes up, and we do the 5 Why’s, the finger always points upward. There is little to no insight downward at what part the team or middle management plays in the “dance” that is occurring within the organizational culture. And the discussions can become quite dysfunctional and we end up with many of the behaviors that I’ve identified.

I think all coaches should enter an organization with full respect for all levels in play. We can’t simply empathize with the teams and ostracize the leaders or vice versa. We need to take a very holistic and balanced view to things. And yes, even when poorly trained or intentioned leaders are negatively impacting our efforts, we need to respect and then engage them; rather than marginalize them. I’ve found that this partnering approach and the requisite balance a much harder stance for many enterprise level coaches. Perhaps that’s why many avoid it and simply focus downward.

Avoiding “Silver Bullets”

There is a propensity at the senior leadership level to try and solve tough transformation situations with tools and models. Scaled Agile Framework is the latest one of these. For example the thinking goes—all we need to do is purchase the SAFe implementation from Rally and we’re three quarters of the way towards agility.

Certainly good coaches leverage tools and frameworks, BUT they also discuss the hard work aspects of organizational agile adoption. They bring in the team and culture changes as aspects that tools and frameworks don’t necessarily hit on all aspects of a balanced agile adoption. In fact, my personal bias is that coaches should lead more with basic practices using cards and walls, before encouraging their clients to introduce tooling and models too early.

Another bias is that we often forget to bring in technical practices at the team level. So instead of coaching Scrum at the team level, we should be re-introducing the team to Extreme Programming practices and raising the bar within programming craft.

Side-by-Side Coaching

There’s nothing better than sitting down with a leadership team and helping them to craft a more agile strategy to a hard problem. For example, when I worked for iContact one of our challenges was aligning our annual strategy with our product roadmaps and our team alignments. This is what I would call good, old-fashioned portfolio level investment and organizational growth planning.

Many agile coaches “steer clear” of this level of engagement, either concerned that they’d have to deal with real-world constraints, or they lack the experience, or they’d have to “work with” management. And “it depends” would be a very unsatisfactory response in these planning sessions, even thought it does depend. BUT, this is a wonderful opportunity for situational coaching, side-by-side with the leadership team. You can remind everyone of core agile principles while you work through various scenarios.

What’s in it for Them?

I like to emphasize and reemphasize the core aspects of agility that are “in it” for leadership—or the WHY behind moving to agility. This takes two forms, what it IS about and what it ISN’T about. For example, agility isn’t necessarily about speed or getting more done or hitting a list of 100 requirements. It’s mostly about quality, customer connection, value, predictability, making thoughtful adjustments, and transparency. It’s also about morale and team engagement.

If the latter things are of interest to the executive and leadership teams, then try to connect the dots daily between these points and how the leaders need to invest in increasing them. And please, this isn’t a one-time presentation or class; this requires situational awareness and a consistent focus.

True Innovation

While I was at iContact, we invested in something we called Innovation Days or iDays. We carved out a few days each release and asked the teams to work on projects that they felt were impactful to our business and customers. We ran iDays for over two years and our Product Owners kept track of the work that resulted.

Over 60% of our iDays projects or initiatives made it into the product. And the majority of these things wouldn’t have even surfaced if we hadn’t engaged the creativity and innovation within our teams. And you have to be consistent with it, you can’t drop the iDays when your plans are behind schedule or the going gets tough. As leaders, the coaching is toward consistent investment and the message it send to the teams.

Don’t Tell

One of the biggest mistakes I see at the leadership level is we all want to be overly involved in what our teams are doing, team decision-making, and telling teams how to react to their project challenges. It’s human nature I suppose because its been the primary mode of operation for most leader their entire career. However, telling the team what to do is very detrimental in gaining a true agile mindset. And achieving that mindset is what drives the results.

And stopping telling entirely is a problem as well. Coaching with a focus on knowing when to step in and when to step out is critical learning for most leaders moving towards agile contexts. And the only way to learn this is situationally – by example and then via peer-level coaching.

Morph Your Metrics

One of the first things I’d like to see every organization take on that is going agile is drive a discussion surrounding how their current measures should and will change. Far too often measures aren’t changed, normally because they’re tied to organizational project progress and people measurement. There’s also reluctance because many leaders would like to lead by dashboard vs. leading by interaction, transparency, and direct engagement. Yet, these are the very ways they need to be changing.

An early coaching focus on morphing metrics can be very useful in guiding an organization forward as well as the cultural changes surrounding engagement vs. dashboard only leadership.

Less Certification Classes and MORE Situational Coaching

We’ve had a tendency in our profession to run lots of certification classes as part of our effort to move organizations towards agile practices. The classes are typically focused towards the teams than upwards. I think we have to reduce the frequency of the classes and balance their focus—upwards, outward, and downward.

At the same time, we need to move from a class model to a situational coaching model. Certifications are great for experienced practitioners, but new teams need role models and examples. They need sounding boards. And they occasionally need someone to tell them which way to go. This is the same for leaders who are involved in these transitions and our coaching needs to focus much more on their needs and transformation. Think of it as “Coaching the Coaches”.

This is the final “installment” in a series where I try to make the case for agile coaches (and trainers) refocusing their attention more towards organizational leadership and management. That would be independent of “how good” we think the managers are.

That we focus on partnering with all aspects of organizational leadership. And that we might, if they don’t engage with us, look to “Say NO” more often helping the make the shift to agility.

In other words, we insist on gaining better leadership engagement and awareness BEFORE engaging their teams and any agile transformation.

I know, I know, this may cost us revenue. And it will likely eke into the number of certifications we’re granting. But under the mantra of “Transforming the world of work”, I think this is the only congruent strategy that we can engage in.

Stay agile my friends,


A few recent blog posts that surround coaching and leadership themes:

  1. We’re Going Agile – Fire ALL of the Managers
  2. Roles & Responsibilities – Do we Need Such Things for Agile Teams?
  3. Agile Coaches – We’re Coaching the Wrong People
  4. What the World Needs is MORE Prescriptive Agile Coaches

Leave a Reply