How to Manage On-Demand Talent in Your Business, Part 2

May 27, 2021
How to Manage On-Demand Talent in Your Business, Part 2

Leading and Managing Internally

This blog post is Part 2 of our two-part series, How to Manage On-Demand Talent in Your Business. You can read part one here.

At Bolster, we’re flipping the script with how CEOs build and augment their executive teams with on-demand CXOs. Through new models of “surge staffing,” bringing on external advisors, and recruiting subject matter experts for short-burst periods of project-based or interim work, we believe CEOs can scale their businesses even faster than before. And this means a new approach to people management.

In our first post, we addressed five tips for CEOs to onboard and set the stage for on-demand executives in their business. It’s critical to make sure everyone is aligned on what that executive was hired to do.

But if this is your first time managing an interim or fractional employee, you might be scratching your head with the best way to go about it. How can you collaborate without taking up too much of their time? How can you make the most of their expertise without overwhelming your current team? How can you encourage them to move quickly without micromanaging?

As with all management techniques, there’s no “one size fits all” approach to managing on-demand talent, but between our Bolster member and client community, and the client base of executive coach Mariquita Blumberg, we’ve observed a few things that seem to set up CEOs for success.

Here are five ways we’ve seen CEOs find effectively lead and manage on-demand executive teams internally.

How to Lead and Manage an On-Demand Executive

  1. Come Up with a Management Plan
    You wouldn’t hire a new full-time executive without a plan. And, however short the engagement, you shouldn’t hire an on-demand executive without one, either. Before Day One, be sure to give some thought to the organizational norms and how you envision the new recruit coalescing with the existing team. Will they attend all team meetings? Do they need 1-1’s with anyone? How will you expose transparency internally to the work they are doing? Setting a management framework that includes regular check-ins is key, and you might also consider a way to gather some skip-level feedback. One last element to incorporate in your plan is what the on-demand is authorized to do in terms of budgeting, decision-making, and setting strategy. While it may feel overly pragmatic at the time, establishing some baselines before incidents become issues will just help to set some guardrails in place early on.
  2. Encourage Them to Say the Hard Thing
    Let’s be real: The longer you work at a company, the trickier it is to be objective and view the business with an outside lens. One of the biggest gifts that an on-demand exec can offer is the gift of perspective. They see things without the rose-colored glasses of someone who’s been under the hood for months on end. The best relationships between CEOs and on-demand executives are ones where the fractional or interim hire is encouraged to share direct feedback, ask tough questions, and make bold recommendations. This doesn’t mean you have to say “yes” to every suggestion (or actively encourage them to “blow up” the organization), but it is important to give this individual the headroom to use their own experience and incorporate the pattern recognition that you might not see from your vantage point. Don’t forget: You brought this individual into your organization to identify (and ultimately help fix!) a problem you couldn’t do on your own. Let them do their job.
  3. Push the On-Demand Exec to Have a Bias Toward Action
    Often when transitioning jobs at the leadership level, common practice and literature encourages executives to spend most of the first 90 days on a “listening tour” to take in as much as possible before making any large decisions. While this makes a lot of sense for a full-time role, this is the opposite of what’s needed in a short-term, on-demand capacity. After all, you can’t spend 90 days acclimating to the job when the entire assignment may be 90 days long! Assuming you have already achieved alignment internally about what that individual was hired to do, you’ve already done the work upfront of determining what is and isn’t on the table. Stress to your existing team (and to the new recruit) that the goal is to make decisions quickly and move past the acclimation stage as quickly as possible. Some of the most seasoned on-demand execs in the Bolster network say they start injecting value into the businesses they advise in as little as one week – or even in a single day! With a bias toward action, you’ll keep everyone focused on moving forward, even if the velocity may feel a little uncomfortable or unfamiliar.
  4. Keep the Swim Lanes Clear
    Remember: You’re not hiring on-demand execs to be full-time employees, so in all likelihood, they don’t need to be embedded in every level of the organization (or take on every aspect of the executive role). The only way that your new recruit can be successful is if they have clear swim lanes to do the job you hired them to do – and not much else. As a CEO, it’s your job to keep a lookout for murky waters, which includes team members who pull that new exec in multiple directions, solicit feedback on unrelated assignments, or take too much of their time on potentially distracting projects. Depending on your arrangement, it’s possible that your new recruit is also working on several other projects at the same time, so the time they spend with you is precious. Be clear with everyone on what you’ve asked the on-demand executive to do (and what’s not in scope). This may mean defaulting to fewer (rather than more) all-team meetings. And yes, it also may mean that your new hire sometimes needs to work with less organization-wide visibility than you’d prefer.
  5. Make Sure They Know When the Job is Done
    By definition, on-demand executive work is temporary. This means that every job has a beginning, middle, and end. But the end is often the trickiest part of the engagement. In the case of an interim role, where a CXO may be filling in on behalf of an absent executive, the time span is likely quite clear with a defined start and end date. But in the case of fractional, project-based, or advisory work, the deadlines aren’t as clear. We encourage CEOs to do their best to establish benchmarks for success early on and revisit these every month, or at least on a quarterly basis for longer-term on-demand engagements. Ask yourself, what is “done” and what does it look like? What’s the downside to the business of leaving them in the job for too long, and how will you recognize when that might be happening? Remember: The goal of this person is to eventually displace the need for them. Don’t be afraid to say when things are done.

The more common it becomes for CEOs to leverage interim, fractional, or project-based talent at the executive level, the more we’ll continue to hear stories and tips from the ground on what works best to integrate this type of worker into your organization. If you have experience successfully managing on-demand executives, we’d love to hear your story too. Email us at for a chance to be featured on our blog for a future story.

-Bethany Crystal and Mariquita Blumberg, May 27, 2021