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Date before you get Engaged: How to Jumpstart New Execs as On-Demand Workers

August 10, 2021

All too often, we hear from CEOs that they are desperately busy, and need someone to quickly take important responsibilities off their shoulders. It’s the life of a startup, right? Yet, this means that they also don’t have time for a long interview or onboarding process when bringing someone in to take on some of that work. We hear from CEOs that they often put off hiring due to the length of time they need to put into interviewing and onboarding.

Enter the on-demand executive consultant. On-demand executives can fill key gaps for startups when they don’t have a need (or resources) for a full time executive. And, getting an on-demand executive onboard can be a quick process, both in the interviewing and onboarding phase. Done correctly, we’ve seen CEOs on Bolster go from job spec to start date in as little as a week – a massive difference from a traditional full-time executive search. Here’s how:


Even though interviewing is a standard approach to hiring, there’s a lot of research showing that interviews, especially unstructured interviews, are not the most reliable or valid method of selecting the best candidate for a role. A structured interview can be a good part of a hiring decision but, according to this article, a work assessment is over 65% more valid than an unstructured interview. Let’s be honest, most of us think that we are better than the average interviewer, and can actually tell in an interview if a candidate will be successful. But, what if there was a way to supplement the interview process? A process that replaces a lengthy series of interviews which may end in mixed results?

We’ve observed that when CEOs ask on-demand executives to complete a project prior to engaging in a longer-term relationship, they find more success. Think of it as a paid audition. After reviewing over 100 successful candidate placements in the Bolster marketplace, we recommend that CEOs approach the hiring process like this:

  1. Review candidates who were selected based on CEO’s criteria for success.
  2. Schedule a 30 minute meeting. Set the stage for what’s needed at the company and ensure good communication fit between the executive and the CEO. If it seems like there’d be a fit, move to the next stage. If talking with more than one candidate, use a structured interview process where you ask the same questions of each candidate.
  3. Ask executive to write a short proposal for the initial project work that includes success measures.
  4. Engage executive for the project. The best projects are scoped for under 30 days and incorporate plenty of time for feedback and determining mutual fit.


Onboarding a new executive into the company is typically complex and time-consuming. They need to fully understand the business context, the culture, the people, and the history. Popular business books such as The First 90 Days encourage new executives to spend a full three months onboarding prior to making meaningful changes. But there isn’t time for that in an on-demand environment – and that’s a big benefit. Because many of our members are experienced in working in on-demand roles, they can quickly onboard into new companies and make an impact immediately. We’ve found that they’ll learn the most important things they need to know about the company simply by doing the project.

When we suggest that CEOs skip the time-consuming approach to onboarding and start with a project, we hear comments like, “Oh - you mean date before you get engaged?” or “walk before you run?” Yes! That’s exactly the approach we see that can work to predict a good long-term fit. To kick off a project, you’d only need to share things like a high level company overview, context for this project and access to the people needed to complete the project. Communication about the hire is more simple too, as it’s starting as a short-term project.

The other benefit of a project-based approach to onboarding is that it lowers the risk for a CEO. If the fit isn’t there after the first project, you haven’t wasted a month in the interview process, and instead have a completed project. The resulting conversation is also easier. Instead of having the difficult conversation as to why you are letting someone go, you simply say ‘thank you’ for completing the project, part ways, and find another candidate.

Changing the approach to executive hiring and onboarding can help CEOs to scale their leadership team effectively by bringing in the right people at the right time for the right length of time. It will also allow you and the executive to test out the relationship before making a longer term commitment. It may not be the solution for every hire, but think creatively about whether you can incorporate more valid selection methods into your hiring decisions.

What to make on-demand talent work for you? Sign up as a Bolster client and start browsing talent today!

-Cathy Hawley, August 10, 2021