The PivotDesk Blog


BTDT: The most difficult decision I’ve made as PivotDesk CEO

When we launched the #BeenThere series we promised to be candid and transparent. We promised to focus on the less than sexy stuff that actually impacts our success and yours.

Why? So that we can all STOP solving the same problems separately and leverage each other’s experiences instead.

When we promised that, we had not planned for this.

It’s still fresh and to be honest, I hesitated on whether or not it made sense for this — but to not share it would be disingenuous. So, I’ve moved the topic we planned to cover for our first #BeenThere post aside in an effort to support our promise of complete and total transparency.

And here you have it…

There’s been a shift in our business at the core of our team.

Kelly Taylor, Co-Founder and VP, Product for PivotDesk is transitioning from the team.

He wrote a painfully honest note about it. You can read his note here.

What happened with Kelly was interesting – unique from my prior experience. Here’s a snippet from his letter that tells you in his words what happened:

“Over the past six months I’ve lost the confidence of my teammates. After talking with mentors and friends that have seen this over and over in companies and not hearing a single story of a situation like this turning around and being wildly successful, we knew a hard decision needed to be made.”

Kelly then goes on to recap feedback from some of our execs that (in short) sounded a bit like this:

“No one really knows what you do anymore.”

I won’t let Kelly take the blame for this. Between he and I, there was clearly a gap in communication to the team.

Kelly had taken on too many roles and splitting his time between them wasn’t translating well within the team. While we needed his undivided attention on product, there were a number of co-founder responsibilities that took him away from this and ultimately left the team wondering why product wasn’t moving at the pace it needed to be.

We let this go on for too long and eventually we hit a point of no return.

As the CEO, I want to make clear how much of an unbelievable struggle this decision was. Kelly and I have fought side by side since the start to build this company into what it is today. Below, I’ll share with you some of the factors that came up and how we dealt with them.

On making hard decisions.

I often say that passive aggressiveness kills companies. I have seen it first hand, and been guilty of it in the past.

At PivotDesk, we make a ton of hard decisions every day. We evaluate our opportunities, derive solutions and implement decisions with purpose.

But then there are outliers like this one…

The decisions we’re often guilty of shying away from.

These are the ones that have the most intense impact on the business and the people in it. They are complicated and our usual process of evaluation NEVER works in these cases.

I’ll tell you why…

Because these decisions come from your gut.

As I’m sure you can relate, there are pluses and minuses with any outcome but in the case of these types of decisions, you generally know what you need to do. Unfortunately, what you need to do often sucks and as a result, you try to avoid it. You try to rationalize your way out of it.

You can’t. And if you’re surrounded by the right people like I was, they’ll remind you of that.

You must stop running from it and implement. Even if the reality is harsh.

Do it for your team.

When you have data and/or the feedback that indicates a trend the way I did here, ignoring that trend, or choosing not to deal with it, will come back to haunt you many times over. I knew that no matter how difficult the decision would be, I had to make it and move forward — it’s the ONLY way to keep everyone focused and driving towards the end goal.

Whether you want to believe it or not, the whole team sees or senses any passive aggressive bias from leadership. That’s not a good thing. Ever.

At PivotDesk, team dynamics are just as important as product, marketing and development. I try my best to deal with them just as quickly and decisively as I do the others. That’s what Kelly and I did here.

The logistics.

In Kelly’s note, he gives you a look at some of the things that drove us to this point. For those of you playing multiple roles in the company or letting tunnel vision cloud your interactions with your team, take a minute and consider how this affects your ability to perform ­and collaborate.

If you’re on the other end… if you’re the one who needs to make the hard decision, here’s a look at how we handled ours.

#1: An open dialog

Kelly and I are lucky to have the type of relationship where we can be incredibly honest with each other. But it takes effort to maintain that type of relationship. We put a lot of energy into remaining honest during this. It’s harder than it sounds. Looking a friend in the eye to discuss the hard stuff sucks but I’m glad we did it. Approaching the issue this way meant we were both aware of things as they were shifting within the team and ultimately that we would decide on the solution together.

#2: “Research”

Kelly and I both put in a period of what I’ll call “research” before making any real decisions. We spoke with our board and our most valued mentors. We did NOT however, go to them asking for a solution. We went to hear about their experience. We wanted to get insight into similar situations they’d experienced in the past so we could then walk away and apply them to a solution that made sense for our situation. (Similarly to what I hope you’ll do with this post should you ever find yourself in this situation).

#3: Involving the team

We actually chose not to pull the team into this decision. Kelly and I have and will continue to be a united front. So while we were receptive to the team’s opinions and experiences, we made sure to support each other publicly while we worked to figure out the best solution privately. To be totally honest, this was both good and bad. The negative was that I don’t think the team (including my execs) believed they were being heard. Because I wasn’t discussing the work I was doing on the backend to find a solution, it may have looked like I wasn’t processing or acting on their feedback. That was a struggle – but because of the magnitude of this decision, I needed to step away with their feedback and decide on the right plan of action separately… with the help of the mentors I mentioned above who are somewhat more emotionally removed from the situation.

#4: Filling in the holes

Kelly’s departure meant we would be without a Product lead and considering the pace at which we’re moving, that’s a problem. A big one. But I couldn’t let that stop us from making a change. I didn’t want to apply a temporary Band-Aid or rush the process and risk ending up with a square peg that didn’t fit. So instead of hiring someone to take over Kelly’s role, I took a step back and evaluated the need. Now we’re looking at a role… a resource… that’s less focused on visionary insight and more focused on implementation. We have a LOT of experience with our market and the problems we’re solving. At this stage, the focus is execution. And we’re bringing someone in to make sure we do exactly that. (More on this later…)

But that’s enough of the rational dissection – now for the human part.

This really fucking hurts.

Soon after starting PivotDesk, I would imagine Kelly and me years from now, sitting in our rocking chairs (Balvenie PortWood in hand) reminiscing about how awesome the journey was — how many incredible companies and people we had the chance to work with.

I have faith we will get there, but I will miss having someone standing across from me in the office who knows instinctively when I’m frustrated or worried about something. I will miss having someone I can talk to about how freaking hard this is and having them intimately understand the reality.

To be totally transparent, I’m most upset about the fact that I’ll have one less person around who wants this as much as I do. One less person that knew what it was like when PivotDesk was just a PowerPoint presentation.

But like many decisions we make in life, our selfish desires aren’t always the right way to move forward. And after pounding your head against the wall enough times hoping the pain will go away, you realize that it might just be the pounding that’s causing the hurt.

Kelly and I learned the hard way. My hope is that in sharing our experience, you won’t have to.

Remember, everything you say or do matters.

Now go build great shit.

And if you have extra space in your office, please consider posting it on PivotDesk to help out other great companies that need a place for now. You never know how much value you might get in return.


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