3 Lessons from a Struggling Sales Function
I'm a sales-driven CEO through and through.
One of my unique abilities (and honestly, there are only 2 or 3 of them) is sales. I’m great at closing deals, but I’m also great at coaching deals.
When I ran my student painting company, I turned hundreds of college students into sales managers who had to do everything from cold pitch potential customers to handle contract negotiations.
The ones who followed my guidance crushed their sales goals every summer.
But in the last few months, I've realized something. My consulting firm didn’t have an amazing sales track record. We didn't have systems and processes the way we did when I was coaching dozens of college kids each year.
Somewhere along the way, I went from being an intensive sales trainer to being a CEO.
And I suppose because I had always been strong at sales, I assumed my skills would somehow transfer through….osmosis?
I've spent plenty of time coaching individual deals, and I’m still very active with our consulting team in that regard.
But I haven't been as disciplined about making sure we have a system, processes, and ongoing, formalized training to ensure that every member of our team involved in sales knows what to do and how to do it well.
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If you're wondering how I could be totally oblivious to this problem up until now, I'll tell you: I wasn’t.
This is a good example of a situation business leaders encounter all the time. You can only deal with so many problems at once. In this case, the first thing we had to tackle was building up our pipeline. Once we started doing that successfully, we were able to dig into the sales side of things. We finally had enough data to see what was and wasn't working.
I knew we weren't doing enough sales training and that we needed to strengthen our sales function. But it wasn't until more recently that it became one of the top priorities for us to manage in the business.
Lesson #1: Be aware of all the problems in your company, but ruthlessly prioritize the ones that matter most. Believe me, the other problems aren't going away. They will still be there when they become the highest priority issues.
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One of the reasons we don't have enough sales training inside the consulting business is, ironically, related to my own expertise in that area. I look at sales training like it should be the basics of how to do business. I've had the wrong expectations for what my consulting team and my sales team should already know how to do.
It's obvious to me because it's my area of expertise.
Plus, I had been regularly coaching deals. I didn't realize that coaching individual deals wasn't translating into broad frameworks and ways of working.
We needed more focus on the basics of sales skills.
Even things I took for granted, like using an assumptive close, never leaving without having a next meeting booked, and making sure the right people show up on the call…they might seem like basics to me, but they aren’t to everyone else.
I can be mad about that. Or I can do something about it.
Lesson #2: Don't mistake individual coaching for systematic training that covers the fundamental skill set you need your team to have.
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At scale, my approach—closing business for the company via individual deal coaching—breaks. It was useful up to a certain point, but I can confidently say it has now broken. The old way of doing things has long since passed its usefulness. We need more structure, and I need to spend more time on other parts of my role.
When a CEO hangs on in an area of their own strength, that area of the business often suffers.
It’s the sales leader who doesn’t quite build a sales function that can stand on its own. It’s the product expert who is still in the minutiae of features, UX, and development sprints. It’s the operations whiz who can’t quite get out of the weeds to focus on the strategic vision for the company.
It’s painful, doubling back to an area where you’re already strong. It’s more painful to recognize the thing you thought would always be a strength has become a weakness, specifically because you have held the company back.
Your company needs more than a CEO doing some other role part-time. It deserves somebody’s full focus, and that somebody should not (more than likely) be you.
Lesson #3: The areas you are naturally good at are likely to be your biggest blind spots. Make sure to invest in those areas as independent business functions, because eventually, your skills will become a blocker, not an enabler.
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Honestly, I’m grateful.
Every problem I have in my own companies is a reminder of the real entrepreneurial experience. The challenges we face are the same ones our clients will face. I have never wanted to be some consultant who says all the “right things” but has no idea what it takes to run a business.
Today, it’s sales training. Next quarter, it will be something else. New obstacles means we’re growing in new directions, and that, ultimately, makes me very happy.
PS - Stay tuned, because I’ll probably do a follow-up on this topic in a few months. We’re going to turn from a team that was capable of selling into a team that’s great at it.
