Woman during job interview and four members of management

7 Deadly Sins of Executive Recruiting

by Jason Ewell

Jason Ewell is as a Venture Partner at Insight Venture Partners, working as a talent and operating partner with CEOs and their teams to accelerate growth, scale operations and build organizations. Prior to joining Insight, Jason was Executive Vice President at TravelClick, where he managed their data, software and marketing services businesses.  Jason previously spent 14 years at American Express in the Commercial Card and OPEN Small Business groups, where he launched new products and helped transform Amex’s demand generation, inside sales, digital and partner channels.  

The further up the leadership ladder, the more critical it becomes to find the right talent.

That’s largely because executives do more than manage; they set the tone, build the culture, make defining decisions and drive strategy. Few things will have a more powerful impact on business success than the executive team, so hiring mistakes at the executive level can make or break a business. Through my own experiences, and working with experts in executive recruiting, I've found the following to be the most common mistakes made by high-growth companies.

1) Failing to create an explicit scorecard.

Creating a list of fifteen skills required in a candidate and then expecting a candidate to have all these, is a common recruiting error. Instead, before starting a hiring or search process, executives and stakeholders should draft a scorecard of three to four critical skills or traits that a candidate must excel at to be successful in the specific job at hand. It should also include a few other valuable traits that are of secondary importance – nice to have, but not essential for the position.  

Having this scorecard will ensure that the hiring team agrees on the core requirements and can measure candidates as objectively as possible. Without one, teams typically get locked into circular debates about the suitability of candidates because each interviewer brings their own ideas to the table about which skills are most important; with no clarity, each candidate suits someone’s requirements, but no candidates are evaluated against the skills that really matter for the business.

2) Looking for the cheap and easy candidate.

Too often when it comes to recruiting talent, executives rely solely on their personal networks, rather than expanding those networks with unknown candidates. There are two risks associated with this strategy. First, executives often do not objectively evaluate their own network, or referrals, against their scorecard. In addition, they may also be assessing an individual based on past performance – their history with the candidate – rather than taking a fresh look. It’s essential to put referrals through the same process as all other candidates. And while it’s expensive, the best retained search firms will expand your universe and challenge your known network.

3) Over-delegating the search.

Hiring leaders make the mistake of delegating too much evaluation and selling responsibility to their direct reports or the search firm.  Executives should remain personally involved in defining the most critical skills, evaluating candidates for these capabilities, and be willing to personally reach out to the highest quality candidates to sell them on why they should join the company. In the first few weeks of the search, hiring leaders should speak directly with the front-line recruiters to review resumes and get a feel for the market. Regular reviews and post-interview evaluations are also important parts of staying engaged, and owning the search.

4) Not having a candidate value proposition and engagement strategy. 

Executives and their search teams should define what makes the company and this position attractive as well as define for whom it would be attractive. It’s equally important to get executives excited about filling the position and to find internal leaders who can describe the company, culture and opportunities because top candidates want to talk to other executives, not exclusively to HR or the search firm. Hiring leaders are the best at describing the role and persuading top talent of the opportunity.

5) Hiring primarily based on pedigree or experience.

Executives like to ensure that candidate profiles check certain boxes.

For example, they may prefer to hire a candidate who's been a CFO in the past, a candidate that attended a specific school, or someone that was referred to them by a trusted colleague. Focusing solely on a candidate's pedigree or experience can lead to a false sense of confidence because candidates may end up being better on paper than they are in practice. It can also lead to low team diversity. This is where the scorecard, a structured interview, and thorough reference checks against the scorecard can improve the quality of hires.

Cultural fit matters just as much as experience. Just because a candidate did something well before, does not mean they will do it well in your setting. After the initial interview and skills evaluation, candidates should meet with select members of the executive team and the CEO for a deeper assessment of whether their personality and strengths align with what the company needs. 

6) A light process.

Too often, companies make critical hiring decisions after a few one-hour interviews, some of which likely occurred on the phone. Recruiters and CEOs should dedicate two to three hours with senior candidates up-front, helping them understand the opportunity and getting to know them. There also needs to be at least the same amount of time set aside for behavior-based and intensive skills evaluation to measure candidates against the scorecard for the role.

Once down to a couple of finalists, conducting 360-degree reference checks are critical. This means asking a candidate for leaders from their last two to three companies, as well as their peers from every function, rather than just calling the references the candidate provides. References that don't come from a candidates' preferred list are less biased and should make up at least half of your calls. Also, don’t delegate references entirely to recruiters and be sure to take the same structured approach with reference calls as with interviews.

7) Creating a terrible candidate experience. 

It pays to be mindful of the experience from a candidate’s view. At times, executives and search leaders neglect the simple things, such as not taking notes, hosting interviews in noisy places and rescheduling or canceling interviews. Also keep an eye on how many hoops a candidate must jump through – the number of interviews, for example, or the overall length of your hiring process. By valuing the candidate’s time and effort and investing in this process, you will increase your chances of hiring top talent and earn respect for your company’s hiring practices.

Hiring the right executives is pivotal to business success. By avoiding these seven pitfalls, hiring leaders are set up to find, select and recruit the best team members.


Jason Ewell

Jason Ewell

Operating Partner

Jason joined Insight in 2015 as a Operating Partner. Jason works closely with portfolio company boards, CEOs, and their leadership teams on overall strategy, with a focus on go-to-market strategy and execution. Jason currently oversees Insight Onsite’s Talent Center of Excellence, working closely…

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