Transformation Regrets

I was speaking to someone recently that had just finished reading the new book TRANSFORMED, and a question she asked caught me by surprise.  

She was saying how her favorite part of the book was reading the case studies about the companies that managed to successfully transform, and then go on to do some very impressive and innovative product work.  But she was wondering if all the transformations had gone as well as the ones in the book?

I laughed and said that I wish they had, but the truth is not so pretty. I reminded her about all the chapters on transformation challenges and the root causes of failed transformations.

But after thinking about this, I realized that it’s one thing to talk in the abstract about issues in a company that prevent or hinder transformation, and it’s another to talk about my personal regrets with the various companies I’ve tried to help transform over the years.

I can’t speak for other product coaches, or even my SVPG Partners on this (although I’m pretty sure they each have their own list of regrets), but I can certainly tell you about mine.  This is by no means an exhaustive list, but I would say these are my major regrets:

Not Being Tough Enough

In truth I made this mistake for quite a few years.  

I would often see issues that I was pretty sure were real problems, but I didn’t know if the problems were serious enough to truly derail a transformation, or if I was just being too idealistic.

I didn’t have the confidence because I did not yet have the experience or the evidence to know that something was or wasn’t going to happen.

This is really the difference that experience makes.  Over time, you learn what is critical and what is not.  Which battles are worth fighting, and which ones that can be safely ignored.

Some inexperienced product coaches make the mistake of treating everything as absolutely critical to fix.  I made the opposite mistake of hoping that some of the serious problems were not that big of a deal.

Being Too Tough

But it’s also true that in other cases, I regret having been too tough.

Some people really don’t have the appetite to address the real work of transformation.

Once I had accumulated the experience to know what was really required to succeed, I would sometimes make the mistake of overwhelming the product leader.

An important lesson I learned is that many people say very sincerely that they know they need to transform, yet they often have no way of knowing what that truly means.  

It’s one thing to say “we know we need to transform,” but that’s very different from “we know what we need to do in order to transform, and we are willing to do it.”

I learned that once you’ve done an organizational assessment, and you now understand the specific areas that need to be addressed, it’s important to be very honest and clear with people about what they are in for, if they decide to proceed with a transformation. 

There have been several occasions where I have done an organizational assessment, and I ended up telling the company leader that I didn’t believe they would be willing or able to do what is necessary, and they would be better off saving themselves the effort and cost.

In other cases, after I shared what needed to be done, it was very clear that this was not what the product leader had bargained for, and that they were genuinely scared of what these changes would mean to them, and if the rest of the senior leadership team would be supportive.

The bottom line is that it is easy to end up being too tough, and it’s important to realize that sometimes the product leader needs some time to wrap their head around the work that needs to be done.

Agreeing To Just Provide Product Management Training

This is a common one, especially in very large companies. So many companies equate “transformation to the product model” with “product management” or “product management training.”

I’m really not sure where this problem originates from, because I think I’ve been very vocal about this for literally 20 years, but for whatever reason, many companies believe that all they need to do is get their product managers some modern training.

And invariably these places do need to raise the bar on their product managers.  But I’ve never seen a situation where this was in any way sufficient.

As I hope everyone that reads these articles knows, product managers don’t create products; product teams do.  

So transforming to the product model means showing product managers, product designers, and engineers how to work together to effectively collaborate on solving hard problems.

If you raise the bar on the product managers, but the product designers and engineers aren’t willing to also change how they work, little will have been achieved.

And even when the product teams are working together effectively, can they really do what they need to without strong product leaders doing their part on product vision, product strategy, team topology and coaching their people through difficult situations?

But many companies believe that the rest of their organization is working fine, and the problem really is just their product managers.

Invariably, these product leaders were hoping for an outcome that I was pretty sure they were not going to achieve, and my regret here is when I’ve agreed to just train the product managers.

Today, when companies tell us that all they want is PM training, we usually explain to them that we’ve learned that this just isn’t enough to cause the outcome they want.  

Sometimes they reconsider and end up broadening the scope of their transformation work, but sometimes they simply go to someone else that is willing to do just the PM training.

When The Company Is Not Willing To Make Tough Calls

Inevitably in the course of a transformation, the company will face some tough decisions.  

Maybe the company is trying to do too many things at once, and it needs to focus.

Maybe a CTO is simply not willing to change.

Or maybe there are some people that are not willing or able to learn their new role.

It’s natural and understandable that the company will try to avoid dealing with such situations, and search for some way to avoid the issue.

My regrets here come from the cases where I could see them working to avoid dealing head-on with the issue, yet I would not call them out on this.

But these are the moments that will make or break the transformation.  I’ve learned it’s essential to identify these moments, and point them out to the leaders, and try to help them clearly understand what’s at stake.

Ultimately of course this is their decision to make, but this is why it’s so critical to have the experience to know when something really is essential, and when it’s not that big of a deal.

When The Product Leader Is The Real Problem

This is a very difficult situation.

Realize that it’s normally the product leader that reaches out and asks for help on a transformation – looking to improve the skills of the product leaders and the product teams, and strategies for influencing the senior leaders.

Most of the time the product leader is quite open about needing help, as this is usually their first time leading a company through a transformation, and many have never worked in the product model before.

However, sometimes the product leader has a very different perception of him or herself, or doesn’t think that the changes would or should apply to them.

It’s not usually very hard to spot this situation.  The hard part is how to handle it.

It is very possible that the product leader will simply end the engagement, and instead go find someone that they don’t consider a threat to how they perceive themselves.

It might be clear to me that the product leader needs serious coaching, but since coaching is built on trust, that would need to be established first.

So this becomes a situation of trying to coach someone that may not want to be coached.  I wish I could say I’ve figured out a solid strategy here, but I haven’t.

My regret here is getting myself into a situation where I’m torn between trying to make the company transformation successful, and having to worry about a product leader’s ego.

There have been times where I have had to step back from the product leader. More often, I double down on my efforts to try to build a relationship with this person.  I also share as much evidence and as many examples of the problematic behaviors as I can.  

In some situations, the CEO can help.  In other situations, that’s precisely what the product leader is afraid of.  And sometimes you just have to try to find a creative solution.

Those are the major transformation regrets I have accumulated over the years. If this helps anyone else avoid the mistakes I’ve made, it will have been worth sharing.