How to Manage On-Demand Talent in Your Business, Part 1

Post 1 of 2: Setting the Stage and Onboarding

We believe that the business world is migrating toward an on-demand workforce across all levels of an organization.

The use of fractional, freelance, or project-based talent is now commonplace among individual specialists (see: Upwork or Toptal), outsourced engineering teams (like Andela or Gigster) and even hyper-local, one-off help (like Thumbtack or Taskrabbit). But when it comes to C-level executives, we’re just seeing the tip of the iceberg as this trend evolves. While more executives than ever are looking for some type of on-demand work, there’s not yet a clear playbook for CEOs on how to integrate senior talent into their organizations on an interim or fractional basis.

Today at Bolster, we have nearly 4,000 executives (members) and 700 CEOs (clients) in our network. We’ve seen dozens of leaders successfully integrate interim, fractional, or project-based work into their organizations, and there are a few common areas that seem to set apart the “good” from the “great” CEOs in their approach.

But onboarding and managing an on-demand executive requires a slightly different set of tools from your CEO toolkit, both in how you set the stage and onboard that hire and how you manage them once they get started.

In this first post, we’ll touch on some tips for onboarding on-demand executives to your organization, drawing from our own observations at Bolster as well as from executive coach Mariquita Blumberg’s advice that she gives clients looking to make a change at the executive level.

Five Ways to Set the Stage and Onboard On-Demand Executive Talent

1. Assess your needs.
   Setting the stage is as important than ever with on-demand hires. Given the short-term nature of assignments (which may range from single projects, fractional work, or even full-time work for an interim period), a thorough needs assessment upfront is critical to ensure success on both sides. At Bolster, we try to help CEOs through this process through initial intake calls where we ask more about the scope of the role, what exactly needs to be done, and what success looks like. If you’re managing this process on your own, you might collaborate with the rest of your executive team to discuss the scope, desired outcomes, deliverables, and budget upfront.
2. Consider starting with a project.
   Depending on the assignment, we’ve seen a lot of success when CEOs “try out” on-demand executives with a project before a longer-term commitment. Projects are neatly scoped, easily measurable, and tend to give everyone enough exposure as to the squishy stuff (“Do we jive well together as a team?”) to decide whether to extend and expand the relationship. On Bolster, we have about 100 projects pre-loaded into our system to help CEOs compartmentalize which aspect of work they need completed. This can be everything from “Create an investor pitch deck” for a CFO to “Conduct an architecture review” for a CTO or “Build a compensation philosophy” for a Chief People Officer. When choosing a project, we recommend picking something that can be accomplished in about two months or less. This way, you’ll have enough time to really get to know that individual’s work style as well as assess the level of quality of their output.
3. Make On-Demand Talent a Team-Wide Conversation.
   One of the toughest parts about bringing in senior-level talent to an organization is the uncertainty that comes alongside it. Your current team may be wondering things like, “Who’s responsible for what?” “What are this new person’s motivations?” or even, “Are they here to replace me?” Some of the most transitions we’ve seen when adopting on-demand talent are when CEOs hedge these questions right off the bat by incorporating their whole team from Day One. Consider posing the question, “What skills do we need around the table to increase our performance by 30%? Who would you all like to learn from?” By introducing this as a collective goal, you’ll be surprised at how quickly the team rallies around the on-demand exec – particularly when they realize their time and expertise is likely only available for a limited period.
4. Identify their place in people management in an organization.
   Perhaps the trickiest area of all to navigate is the interpersonal relationships of people management with on-demand executives. In the case of a project-based or fractional hire, it’s unlikely that this individual will have any direct reports who work full-time at your company. In this case, be sure to clarify their role internally. Are they there to help train your colleagues, to coach them, or to simply offer an external, expert perspective? As CEO, it’s your job to pay attention to any power dynamic disparities that might come up and nip these in the bud before they fester. On the other spectrum, if you’re bringing on an interim executive for a fixed period of time, it’s likely that this individual will take on direct management responsibilities, if only temporarily. This is when management style and team fit becomes crucial for a smooth transition. One thing that may help is to create a “User Manual” – a sort of, how-to guide for working alongside that individual. We have a template on Bolster for CEOs and CXOs on how to get started; our hope is to help organizations move from the onboarding stage to the “getting things done” stage as quickly as possible.
5. Know what you’re not looking for.
   Last but not least, we suggest considering a few characteristics of what you’re not looking for in an on-demand executive. You might consider this to be the “anti-type” (that is, the opposite of the archetype) of your ideal executive. Jot down some characteristics or signals that might signal red flags for that individual and how you might recognize those behaviors in the hiring process. While it’s easier to part ways with an on-demand executive than a full-time hire, it still stings to bring someone into your company that’s not a great fit. Sometimes knowing what you don’t want can help point you in the best direction toward the right fit.

-Bethany Crystal and Mariquita Blumberg, May 6, 2021