How Good Leadership Can Help Bridge Generational Gaps in Small Businesses

If you could create your own fantasy board of directors, who would be on it? CO— connects you with thought leaders from across the business spectrum and asks them to help solve your biggest business challenges. In this edition, we ask a leadership expert for advice on leading a multigenerational team.

In this edition of “Ask the Board,” we feature Shernette Grant, Founder of Unorthodox Leadership Consulting & Management Services, LLC, a national advisory firm that helps organizations strengthen leadership, align institutional infrastructure, and improve organizational performance.

She points out that, for the first time in modern history, up to five generations are working side by side. This has sparked conversations about how traditionalists, baby boomers, Gen X, millennials, and Gen Z differ in the way they think, communicate, and approach work.

Shernette believes many small businesses are asking the wrong question. The question isn’t “How do I manage all these generations?” It’s “How do I lead people whose experiences have shaped very different expectations of work?”

Here are Shernette’s five tips for successfully bridging generational gaps:

Look beyond generational stereotypes

Generational categories can provide context, but they shouldn’t become conclusions about individual people.

Statements such as “Gen Z doesn’t want to work,” “boomers won’t change,” or “millennials need constant validation” may explain frustration, but they rarely help a leader solve the actual problem.

The better approach is to translate what people are actually asking for.

When someone says, “I want flexibility,” ask what flexibility means. When a manager says, “I expect professionalism,” define the behaviors that demonstrate professionalism. When someone says, “I don’t feel respected,” find out what respect looks like to that person.

Words such as “respect,” “trust,” “responsive,” “professional,” “flexible,” “accountable,” and “urgent” may sound universal, but they aren’t.

Strong leaders make the implicit explicit.

Don’t mistake resistance for defiance

When someone pushes back against a new process, technology, policy, or expectation, leaders can quickly label them as difficult, resistant, entitled, or unwilling to adapt.

Instead, become curious before becoming critical.

Ask: What is this resistance telling me?

An experienced employee questioning a new technology may know something about customers, previous attempts, operational risks, or the company’s history that newer employees don’t. They may also worry that years of knowledge and experience are becoming irrelevant.

Likewise, a younger employee challenging an established process may not be disrespecting authority. They may simply see an inefficiency that everyone else has learned to tolerate.

Resistance is information. Strong leaders look for what’s behind it before deciding how to respond.

Bring experience and innovation together

Small businesses need both experience and innovation. 

Experienced employees often bring institutional knowledge, customer relationships, context, judgment, and lessons learned. Younger and newer employees may bring technological fluency, emerging practices, different perspectives, and a willingness to question processes that no longer make sense.

The goal isn’t to decide which generation has the better approach. It’s to find ways for employees to learn from one another.

One practical strategy is reciprocal mentoring.

Allow experienced employees to serve as “context coaches,” explaining why decisions were made, what has been tried before, and what institutional knowledge matters. At the same time, let younger or newer employees serve as “tools coaches,” introducing new technology, processes, and efficiencies.

That way, knowledge moves in both directions, and everyone has an opportunity to contribute.

Turn knowledge transfer into a business practice

Generational leadership is also a business continuity issue.

Ask yourself: If my most experienced employee left tomorrow, what would disappear with them?

Then ask: If my youngest high-potential employee left tomorrow, what future capabilities would I lose?

Critical knowledge shouldn’t live exclusively in individual employees’ heads. Small businesses can create simple practices such as documented procedures, cross-training, job shadowing, reciprocal mentoring, structured handoffs, and brief after-action reviews. 

Don’t wait until someone announces their retirement or resignation to discover how much they know. Knowledge transfer should be part of how the business operates, not an emergency response to someone’s departure.

Set shared expectations before conflict arises

Many workplace conflicts happen because people use the same words, such as “respect,” “flexible,” and “urgent,” but attach different meanings to them.

Hone in on what they mean before they start conflicts. 

Ask:

• “When we talk about respect, what does that look like on this team?”
• “When we talk about flexibility, what does that mean on this team?”
• “When something is urgent, what does that mean on this team?”

Then turn the answers into observable behaviors.

The goal isn’t to eliminate individual preferences. It’s to establish enough shared understanding for people with different preferences to work effectively together.

CO— aims to bring you inspiration from leading respected experts. However, before making any business decision, you should consult a professional who can advise you based on your individual situation.

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