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Hiring of Direct Reports: Responses from CEOs

Nate Lentz
May 26, 2015

Osage Venture Partners recently published a CEO survey focused on hiring and recruiting. After reading the initial results, I reached out to a group of CEOs whose hiring practices I respect to get a sense of the process they go through to hire a direct report. I asked each of 15 CEOS “How much time do you spend with a hire who will be a direct report to you before you make an offer?”. These CEOs included portfolio company leaders and others in my network, all of whom run B2B technology companies. Company sizes range from over $100M down to some of our newest investments. Here are the quotes in no particular order. They do not need any analysis as they speak for themselves but a couple things of note.

  • Hiring a senior executive is a lengthy process involving multiple meetings and many team members
  • Very often candidates are seen in different social settings and with different mixes of people – restaurants, drinks, with significant others. All with the goal of getting to know the person at a deeper level
  • The CEO owns this process – hiring a direct report cannot be delegated

“I spent a lot of time with the two most recent hires out of the office. Head of engineering’s company was acquired and I had to convince him to walk away from his earn out. He turned down our first offer but reached back out with interest a month later. He came into the office 2 times to meet with the team. We met 5 times out of the office for dinner/beers. VP of Sales came to the office 2 times to meet the team. We met 1 on 1 three times out of the office for dinner/beers. We had ~2 hours of phone calls. He spoke with 2 members of the board.”

“It has varied: Folks I “knew from the industry” I have met at least a dozen times and have had dinners/coffees – have even met their spouses – before the formal process which is several meetings and long phone calls plus at least 2-3 visits at the office with the rest of the team. For CFO who was part of a normal recruiting process, I had 2 interviews and several calls to winnow down my list, then I had him come meet the team and had a separate lunch meeting with him. Then in his case I had him meet with three directors too, before presenting the recommendation to the Comp Committee “

“We spec the job and write a detailed job description and key requirements. I review first, usually 90 minutes, broken into two 45 minute periods. I ask questions for 45 minutes, then the candidate asks questions for 45 minutes. At the end they are told that if they pass the rest of the interview process there will be one final interview by me. This is followed by interviews by every member of my direct reports. If it is not confidential, also will do an interview with a couple of employees. Then candidate is told that the final interview will be a discussion about their 90 day plan. They are also offered a phone session with me to get answers to any questions they may have to help prepare. Final interview, review of 90 day plan, digging deeper into the things that were left over from the first interview and items others raised.”

“Process is pretty loose. At least 2-3 meetings and one meal for sure.”

“Great question. I can’t say that I have a defined process for this…probably should. Almost always there would be 4-5 one-on-one sessions; typically a mix of in-office and “social”, at least one breakfast/ lunch (typically earlier in the process) and one dinner (later in the process). The initial get together may be 60-90 minutes; follow on sessions would be 2-3 hours. Having said all that, I still am a bit hesitant to rely on these face-to-face sessions and try hard to find a reference that either I (or a colleague) know or has been sourced independent of the candidate.”

“I was more successful when I recruited, going after someone I knew or who was known by others on the team. I wanted to know as much as possible before a first call. Candidates had at least 3 interviews followed by a meal. First meeting one on one. Next, individual meetings with peers. Each would discuss their impressions with me one on one. If everyone unanimously approved, the next step was meetings with outside Board members. Final meeting one on one to discuss our offer. Also I often had at least three 20 – 30 minute one on one calls during the process.”

“I probably have spent anywhere from 2-3 hours with them. Always a meal. I have a direct report of mine interview with a good percentage of our senior team leads. We also try to focus at first on can this person be successful and not do we like them. We measure against 7 cultural fit elements, and I have my own three filters. Always try for multiple meetings. One thing I have found helpful at the end was a dinner with spouses. Always seems to provide some additional perspective, especially if relocating. “

“First interview with me following headhunter or network recommendation. Then with my other directs on phone and one in person. Phone interviews with key investors. If successful, dinner with me and directs. Finally business case, expectations and contract discussion with me.”

“Spend 8-10 hours of time with me. Usually split over three meetings, a company hour and finally a dinner with significant others. Process is for me to meet first, then introduce to direct reports for interviews (I interview again as well), then do company gathering like a happy hour to get a sense of culture fit, then dinner with me and significant others and finally negotiate terms.”

“Initial phone call 30-45 min make sure like person generally and sell them story. In office meeting with me about hour and a half. If like them…. In office meeting with team about 3 hours (usually meeting with other DR’s), 5-10 min close out with them thanking them, seeing if any major concerns, and telling them will discuss with team and be in touch. If team liked them. Phone call with me catching up about concerns/thoughts on both sides and creating agenda/deliverables for next meeting (they bring some work, they do an analysis of some sort, i produce financials, i deliver product roadmap, etc). Reference checking. In office meeting with me about hour and a half reviewing items from #4 (this may also include meeting some of the more junior members that would be reporting to or working with them). If we’re bought in. Next social event – dinner and drinks – usually with one other person from team. Last decision. This would usually happen over 3-4 weeks. “

“At least 3-4 meetings. Always have a meal. Also do a working session or two. “

“Skype / video interview filter first with me. Then, interview on site with select team second. And me again that round. Get down to two finalists. Then Skype with board member. Two finalists in office back to back for a 3 hour ‘working’ session where we explore real scenarios to get a feel for working together. Me, one other executive. It is a simple filter. If in a 3 hour working session you don’t learn anything or if the candidate reverts constantly back to ‘I’d need to get in and take stock of the situation’ without ever getting specific or giving examples of what has or hasn’t worked for them before? Wrong person. The right one will educate, challenge, and surprise you.”

“Hours of phone calls, multiple in office meetings with me and with team. Sometimes a coffee but usually not a dinner or alcohol event. I actually think the best way to hire a direct report of mine is doing it over a long period of time, because I find that you really can understand where they are coming from and how much of a fit especially a financial fit you have.”

What is your process? – Let us know, we are interested.

One Note: We did not ask for the whole process – do you use a recruiter? How many candidates do you commonly look at? Are references done? The question was time spent in the hiring of a direct report and how that time was spent. Knowing many of these companies, questions on other parts of the process would have yielded similarly thoughtful responses.