Hiring for key roles is one of the most critical—and challenging—tasks any company faces. Traditional interviews often focus too heavily on either a candidate’s strategic vision or their technical skills, rarely offering a holistic view of how they’ll actually perform on the job. Enter the working session: a real-time, collaborative problem-solving exercise that’s redefining the way companies evaluate talent.
More than just another interview tool, working sessions provide a unique window into a candidate’s ability to balance big-picture thinking with tactical execution. Here’s why this method is gaining traction among forward-thinking companies and how it can transform your hiring process.
What are working sessions in interviews?
Working sessions simulate real-world business challenges by immersing candidates in a hands-on problem-solving exercise. These sessions are typically divided into two parts:
- Strategic planning. Candidates discuss high-level priorities and how they would approach key challenges.
- Tactical execution. They then dive deeper into one priority, offering actionable steps and working through the details.
This structure allows hiring teams to assess both big-picture thinking and attention to detail in one session. Think of it as combining the traditional “airport test” (would you want to be stuck with this person for hours?) with a practical evaluation of skills.
Why working sessions work
Traditional interviews focus heavily on candidates’ ability to answer questions or present pre-prepared materials. While these methods have their place, they don’t always provide a clear picture of how someone will perform on the job.
Working sessions force candidates to demonstrate their ability to move seamlessly between strategy and execution. For instance, a candidate might start by prioritizing five key business challenges provided by the hiring team and explaining their reasoning. Then, they dive into one challenge and outline actionable solutions. This not only reveals their thought process but also shows how they handle ambiguity and complexity.
In a typical working session, the candidate engages directly with the CEO, CFO, or leadership team. This interaction reveals how well they can collaborate, respond to feedback, and engage in productive friction—all critical skills for leadership roles.
Unlike take-home assignments, which allow candidates days to prepare polished responses, working sessions evaluate how candidates think on their feet. This is especially valuable for roles requiring quick decision-making and adaptability.
When to use working sessions in your hiring process
Not every role or candidate is a fit for working sessions, but they shine in scenarios where strategic thinking and execution are equally critical.
- Directors or senior managers ready to step into a VP role can prove their ability to think strategically while managing the day-to-day.
- Candidates for CFO or COO roles who need to show they’re still willing and able to roll up their sleeves.
Working sessions are less effective for hyper-junior candidates, who may not have the experience to engage meaningfully, or for overly senior candidates who are too far removed from day-to-day operations.
Structuring a successful session
The beauty of a working session is its flexibility, but the most effective ones follow a structured approach:
- Start with Strategy
Present the candidate with a real-world challenge, such as prioritizing the company’s top OKRs or allocating resources across competing priorities. Ask open-ended questions like:
- How would you prioritize these challenges?
- Which would you tackle first, and why?
- How would you allocate resources to achieve maximum impact?
This part of the session tests the candidate’s ability to think at 30,000 feet and understand the broader implications of their decisions.
- Dive into Execution
Once priorities are set, zoom in on one challenge. Ask the candidate to outline actionable steps, including:
- Who would they involve and why?
- How they would measure success.
- What potential roadblocks do they anticipate, and how would they address them?
Push them to think critically and provide specifics. This phase shows whether they can translate high-level thinking into tangible results.
- Encourage Healthy Debate
Use the session to simulate real-world collaboration. Push back on their ideas, introduce new variables, or challenge their assumptions. Observe how they respond—do they hold their ground, adapt, or shut down? This reveals their ability to navigate friction and maintain composure.
Best practices for hiring teams
While working sessions are powerful, they can backfire without proper preparation. Here’s how to set your team — and candidates — up for success:
- Spend an hour preparing for the session. Identify relevant challenges, clarify objectives, and align on the session’s structure.
- Use real problems from your business, such as quarterly priorities or operational bottlenecks. Authenticity keeps candidates engaged and allows for more meaningful insights.
- Tailor the complexity of the session to the role. A director stepping into a VP role needs different challenges than a seasoned CFO.
- Observe how candidates handle feedback, adapt their ideas, and engage in productive dialogue.
What to look for in a candidate
Working sessions aren’t about finding the “perfect” answer—they’re about uncovering potential. Here are key indicators to watch for:
- Does the candidate prioritize effectively and articulate their reasoning?
- Do they propose actionable, detailed solutions and anticipate potential roadblocks?
- How do they respond to feedback, curveballs, or new information?
- Do they engage constructively and build on the ideas of others?
Avoid common pitfalls
Poorly executed working sessions can lead to frustration for both candidates and hiring teams. Avoid these common mistakes:
- A poorly prepared session leads to vague discussions and wasted time. Dedicate at least an hour to structuring the session.
- Match the session’s complexity to the candidate’s level. Too simple, and you won’t learn much; too complex, and the candidate may flounder unfairly.
- Keep it simple. The goal is to evaluate strategic and tactical skills, not to create an elaborate obstacle course.
The takeaway
Working sessions are redefining how companies evaluate talent. By combining strategic discussions with real-world problem-solving, they offer a clearer, more reliable picture of a candidate’s abilities than traditional interviews ever could.
Working sessions are a powerful tool for companies looking to elevate their hiring process. They test not just what candidates know but how they think, collaborate, and execute—all essential traits for thriving in today’s fast-paced business world.
Ready to implement working sessions in your hiring process? With the right preparation and structure, this approach can transform how you identify and secure top talent.
