Hiring_a_New_Executive_David DeWolf_1200x675

How I Hire a New Executive

1024 576 David DeWolf

Hiring a new member of your executive team is such a key decision. Building your team wisely can put you on a path for rapid growth and success, while one false move can set you back months or even years. 

As I’ve written about before, I don’t believe that the “traditional” interview process is well-suited for the modern workplace (my conviction in this has definitely grown in the 10 years since the original post). That’s especially true when we’re talking about executive-level hires. You can have a thousand hour-long conversations with someone and still not get a great read on whether they’ll be the perfect fit to join your executive team, lead a department or business unit, and help take your company to the next stratosphere. 

I’ve come up with a few ground rules for high-level hires that have been shaped by my experience recruiting, hiring, and working alongside executives for a number of companies in different stages of growth. I always try to follow these ground rules when looking to fill executive-level positions at 3Pillar or companies where I’m on the board.  

Remember that Departures are Opportunities to Revisit What’s Needed

It’s easy to fall into the trap of filling the same seat whenever there’s a departure on the executive team. Let’s say your long-time Chief Sales Officer is retiring to spend more time with her grandchildren. She’s been with your company for 7 years, so she’s had oversight of a large global team that performs a critically important role. The void she’s leaving will no doubt be profoundly felt.

All of that doesn’t necessarily mean that you need to go out and hire another CSO. This is a time for you to reflect and take stock. Surely much has changed with your business in the last seven years. Is another CSO what you need now based on where you are as a business? 

In my experience, the answer to the question above after a departure typically follows the 80/20 rule. Eighty percent of the time, I end up looking for the same (or comparable) job responsibilities. Twenty percent of the time, our business and team have changed enough that we take the opportunity to alter the roles and responsibilities for the next hire. I wrote a 3-part series on Organizational Design recently that may be useful if you’re dealing with an executive departing. Start with part 1: The Fatal Flaw of Organizational Design.          

Spend Time with Candidates in Many Different Settings

I learn far more about candidates by seeing how they carry themselves in different situations and settings than I do by sitting across a boardroom table and discussing the position, their previous experience, and whether they are well-suited for the role.

I always have at least 3 one-on-one visits, each in a different environment, with candidates for these positions. This helps establish rapport, get a feel for one another’s background and communication style, and in general, see what it could be like to work together. Aside from the obvious options of sharing a meal or sitting down for Starbucks, I’m a big fan of going to baseball games, taking walks around the National Mall in DC, and even taking short road trips to places like Annapolis. Nothing will tell you more about a person’s ability to persevere through adversity (and laugh at him or herself) than eating whole crabs.

Just as important as me spending time in different environments with candidates are the group interviews that we conduct with the entire executive team. The most important “team” that new hires will be a part of is the executive team, so it’s vital to land on someone who will be a good fit with his or her peers. In these group discussions, we are looking to make sure that candidates can bring new experiences and ideas to the table. We want to feel confident that they will complement the existing executive team rather than spawn turf wars. And we ideally want to see them in action to stress test their collaboration, vision, and performance under pressure. 

Find Ways to Collaborate During the Hiring Process

Seeing how a person thinks on their feet during the interview process is a valuable indicator of what it would be like to have them on your team. Even if it’s something as simple as brainstorming potential solutions with your team to a nagging problem, that can be enough to give you a feel for what it would be like to have the prospective hire in the room when major decisions are being evaluated.  

Along those lines, a short-term consulting engagement can also be a great way to test someone out for a key role. This opportunity won’t present itself with every hire, but it has worked out well for me on one notable occasion. When Tony Orlando left for a Silicon Valley unicorn in 2016, I was in a bind. Tony had become my right-hand man in the 4+ years he was our EVP of Market & Client Services. He’d had broad purview over sales and marketing as 3Pillar scaled from around $25 million in annual revenue to $50+ million. He was also one of the first people I called when I was thinking through strategic decisions for the company, and he was a key collaborator on more initiatives than I can recount. 

So, I had no idea how we would transition smoothly to life after Tony when he broke the news that he was leaving. Frankly, I had my doubts about our ability to do so based on the scope of his responsibilities. I had an acquaintance at the time, Heather Combs, who had a different background and skill set than Tony, but I had an inkling that she could be successful as his replacement.

I didn’t know how working with Heather would go given that we already knew one another socially, and I’m sure Heather had her fair share of uncertainty as well. We started off with an agreement for her to serve as a consultant for three months while we found a bridge from Tony to whatever would be next. During that time, Heather proved to be an invaluable resource on everything from analyst relations to restructuring compensation packages for the sales team.

Now, over five years later, Heather has become that same trusted advisor that Tony was. She served as our Chief Revenue Officer (aka the “new Tony”) for 3.5 years and our Chief Operating Officer for about a year after a few major acquisitions. She’s now serving as our Chief Commercial Officer, a role that blends the two previous executive roles she has been in. Looking back, I can say with all certainty that her temporary stint as a consultant is what gave both of us the certainty that Heather would be a great fit.    

Listen to Your Gut  

Once you make the hire, you have to be honest with yourself about whether it feels right. No matter how “good” you are at hiring, and no matter how impressive a candidate may be in whatever situation you throw him or her into while interviewing, there are going to be times where what you thought was a surefire thing just. isn’t. working.

In that case, if you’ve exhausted all your options and aren’t seeing improvement, you have to make the tough call to part ways while also respecting what the person may have sacrificed to join your company. While painful and perhaps even embarrassing, it far beats the alternative of watching them figuratively drown in the deep end while also becoming a drag on the company.  

Wrapping It Up – Hiring a New Executive

Hopefully, you don’t find yourself hiring new executives very often. When the opportunity comes along, that makes it even more incumbent on you to make it count. Here’s the best way I’ve found to do so: re-evaluate what your company needs based on the current state of the company. Spend time with candidates in a variety of settings as you get to know them. Find a way for you and your team to roll up your sleeves with candidates as a test drive.

This approach requires some more investment up front from all involved, but the returns you will see down the line make it well worth the time and energy you expend during the hiring process.