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Whether looking for a new job or a new consulting engagement, interviews help me decide whether I want to work with that company and can reveal details about how their business truly operates.
Those conversations can not only uncover the state of their current operations and potential areas of risk or opportunity, but also position you to be a strategic partner invested in their long-term success.
As my latest consulting engagement wraps up, I’ve started thinking ahead to my next client.
I’ll discuss some of the questions I frequently ask and what the answers might indicate about their business:
1. How often do you hire, and how long do people stay?
Understanding the hiring frequency and employee tenure gives you insight into the stability and culture of the organization. If the average tenure is short, it could indicate issues with job satisfaction or the company’s ability to retain talent.
- Average tenure: Is it a revolving door, or do people stick around? Longevity suggests satisfaction and alignment with company values.
- Reasons for surge hiring: Is there a pattern of reactionary hiring, or are they scaling strategically? This could point to growth or instability.
- Layoffs history: Knowing if they’ve had to downsize can tell you a lot about their financial health and how they handle economic challenges.
2. What is the biggest challenge you have today?
Every business has pain points, but identifying the primary challenges your client faces is crucial for offering targeted solutions.
- Hiring and retaining good people: Are they struggling to find or keep the right talent? This could indicate issues with culture, compensation, or management.
- Sales: If sales are lagging, it could be a sign of deeper market issues or internal problems with product fit or marketing.
- Communication/organization trouble: Poor communication can lead to inefficiency and frustration, signaling a need for better tools or processes.
- Lacking expertise in certain areas: This could be an opportunity for you to step in with your specialized skills.
- Funding: Financial constraints can impact every part of the business, from hiring to growth potential, and can indicate a risk to your engagement before you even get started. It can also be an opportunity to shine by helping increase efficiency or cut costs.
3. Do people spend more time working together or are they focused on individual tasks?
The answer to this question reveals the company’s work culture and collaboration dynamics.
- Heavily collaborative: Teams that work closely together may benefit from strong internal communication but could suffer from too many meetings or unclear roles.
- Siloed: If employees are more focused on individual tasks, this might mean they have well-defined roles but could lack opportunities for innovation or teamwork.
4. Are people able to focus on what matters and what they’re really good at?
This question digs into how well the company enables its employees to contribute their best work.
- Distractions by repetitive chores: If people are bogged down by tasks that could be automated or delegated, it’s a sign that processes need improvement to free up time for high-value work.
- Employee well-being: A team that is not just productive but also happy and engaged is a representation of overall company health. Those positive attitudes are infectious and it’s easier to work with people who are optimistic about the future.
- Creating impact: If you’re expected to take on-call rotation, perform maintenance, or run through rote tasks, your ability to create an outsized impact will be reduced until those tasks can be automated.
5. Are there 'everything' people who are critical to operations?
“Everything” people can be both a strength and a weakness. They’re essential to the current operations, but their irreplaceability can also be a risk.
- Sustainability and bus factor: If the company relies heavily on a few key individuals, what happens if they leave? This speaks to the sustainability of operations.
- Toxicity or excellence: Sometimes, these individuals can become bottlenecks, either by holding onto too much responsibility or being so good at their job that the company hasn’t bothered to spread out their tasks.
6. How involved are you in the day-to-day activities of your team members?
A leader’s involvement in daily operations can indicate their management style and the level of autonomy given to employees.
- Ideally, not at all: The best leaders set the vision, remove obstacles, and then step back to let their team do their work.
- Hands-on involvement: If they’re heavily involved in daily tasks, it might suggest a lack of trust in their team or an overbearing management style, which could be a red flag.
7. Can you describe how you lead your team?
Good leaders understand that their role is not just to manage tasks but to cultivate an environment where their team can thrive. Here are some best practices that distinguish effective leaders:
- Recognize their unique role: Good leaders know that certain people and problems require their specific attention. They understand their unique value and step in where they can make the most impact.
- Adapt as a "floater": The issues a team faces change over time, and so should a leader’s involvement. Effective leaders are "floaters," moving to different areas as needed, rather than staying fixed in one role or function.
- Regular check-ins and 1-on-1s: Leaders should conduct regular 1-on-1 meetings with team members, focusing not just on work performance but also on personal health—emotional, physical, and interpersonal well-being. These check-ins are crucial for maintaining a strong, supportive team culture.
- Support career development: A key part of leadership is helping team members grow in their careers. Leaders should actively support their team's development by offering opportunities for learning, mentorship, and career advancement.
- Team building activities: Beyond the day-to-day, leaders should invest in occasional team-building activities. These help strengthen team bonds, boost morale, and foster a collaborative environment.
- Facilitate, don’t dominate: In meetings, good leaders facilitate discussions, ensuring everyone has a voice without dominating the conversation. They guide the team towards decisions, empowering members to take ownership of their work.
Unlock insights with the right questions
When interviewing a client, asking the right questions can reveal much about their company’s inner workings and areas that need attention. Understanding these dynamics not only helps you better serve the client, but also positions you as a strategic partner who’s invested in their long-term success.
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