Strategic Questions That Uncover a Company's Real Culture

Jersey City, New Jersey, USA

“We are what we repeatedly do. Excellence, then, is not an act, but a habit.”‍ ‍- Aristotle, as interpreted by Will Durant for Nicomachean Ethics

When you’re vetting a new partner, a potential employer, or a client, it’s easy to get blinded by what’s glossy. 

Their website is beautifully designed, the values page is filled with curated language, the leadership speaks with polished precision, and the case studies look like an agency wrote them.

But the real culture of an organization actually doesn't live in its brochure website. It can be found in the day-to-day reality of how things actually get done.

I was having coffee with a partner at a high-end law firm. On paper, and in the marbled lobby, everything looked immaculate. But as we spoke, I realized I didn't want the Marketing team’s version of the business. I wanted the operating version of the company. As an executive coach, I wanted to know three things: a) if the strategy was actually coherent b) if people felt ownership, and c) if the team was truly energized.

I came up with this list of 9 questions that pierces the veneer:

1. Company's living values

Most firms have values listed on a wall or a website. Instead, ask: “What are your values and how do they show up?” Note: If they can’t point to a specific, hard decision they made because of those values, they’re just slogans.

2. Strategy

A strategic plan doesn’t need to be a public manifesto. Instead, ask: “Who writes it and who manages it?” Note: If the leadership team can’t answer that clearly, strategy is likely just an abstract concept, not a management practice.

3. North Star

A real vision unifies a company. Test this by asking: “Can your leaders describe the future you’re building in plain, non-corporate English?” If they start using jargon, they don’t have a vision. Instead, they are repeating a slide deck.

4. The junior employee test

Ask the leadership: “Can you recite your top goals for this year without looking them up? Could your most junior employees do the same?” If the answer is no, it signifies a communication problem

5. Communications

Town halls, emails, and offsites are just channels. The real question is: “Does your communication create trust and momentum?” Culture will inevitably suffer if information is treated like a commodity

6. Office Weather

Dashboards track metrics, but they don’t track morale of employees. Ask leaders: “Are people energized by the direction of the company?” The best leaders can read the room before the turnover data confirms the problem.

7. Focus

There are a plethora of ideas at most companies. What is really required in my humble opinion is focus.  Ask: “What have you explicitly said 'no' to lately?” If they can’t name a strategic "no," they aren't protecting their capacity.

8. What is the cadence of strategy?

If the leadership team claims strategy is a priority, ask how much time they spend debating it. If they aren’t talking about the future every single month, it’s not a priority.

9. Big Picture

KPIs, OKRs, and scorecards are important to track progress of the company. The real question is: “Do your people understand how their specific work connects to the firm’s success?” If they can’t see the connection, they are doing busy work, as my old manager used to say.

The Bottom Line:

These questions might seem simple, but they are incredibly difficult to answer for a company that isn't truly aligned.

Next Step: Strong leadership is built on clarity. If you’re trying to assess a potential partnership, audit your own organization, or simply need an outside perspective on whether your culture matches your ambition, I’m available for a 1:1 conversation.