Leading Experienced People: How to Overcome 3 Dilemmas That Make it Hard

What is it about leading experienced people that makes it so challenging?

They know more than we do.  They have been there longer.  They already have their ways of doing things.

Then we walk in and we’re expected to tell them what to do, and when to do it.  We want to produce results sooner rather than later.   And of course we want to prove ourselves as capable leaders in the process.

Leading experienced people presents dilemmas that can be hard to overcome, but by doing the unexpected, we can find ways to forge a strong, productive team.  Here’s how.

Leading Experienced People - How to Overcome 3 Dilemmas That Make it Hard

45 Pairs of Eyeballs

The day I took over my first platoon, I was nervous.  I had all of about eight months experience in the Army.  Most of that time was in schooling and training.

There were 45 pairs of eyes in the formation looking back at me.  As the joke goes, nearly every one of those Soldiers had more time just standing in line at the Dining Facility than I had total in uniform.

In a way it seemed that the natural order of things was upside down:  the young, inexperienced person was in charge.

I no longer remember exactly what I said to them, but the feeling was unforgettable:  a mixture of excitement, apprehension, and a strong desire to do well.

That was my situation 31 years ago, and since that time, it seems nearly every job I’ve held has been full of similar contradiction.  I was rarely the expert, often younger and less experienced, and yet found myself in a position of leadership.

In fact, this situation may be closer to the norm than we realize.  But we should see the opportunity to lead more experienced people as a great advantage, so long as we can overcome three dilemmas that seem to present themselves.

3 Dilemmas in Leading Experienced People

Giving feedback vs. getting feedback.  Part of our job as leaders is to give others feedback so our teammates know how they are doing.  Hopefully most of this is positive feedback, but some of it will have to be critical.  This can feel awkward when working with someone who is older and more experienced.

At the same time, what might be more helpful to us is to get feedback from that experienced person about how we are doing and how the team is performing.

Imposing structure vs. granting autonomy.  As leaders, we can be eager to set goals and performance standards, and quick to demand regular updates and reports so that we can stay on top of things.  Aren’t we supposed to be in control?

But this isn’t the first rodeo for our more experienced teammates.  They may not feel they need our “help,” and our attempts to be involved can come across as micromanagement, or even seem demeaning.  If they are good at what they do, often they just want the space and autonomy to get the job done.

Proving ourselves vs. helping others shine.  And let’s face it, if we are newer, younger, or less experienced, we may not feel very secure in our position as leader.  Respectful teasing of the brand-new lieutenant is a finely-honed craft in the Army.  We want to show that we deserve to be there, and that we can successfully lead.

Yet how do we prove ourselves when we know less than others?  And how do we allow others to show their skills and abilities without forfeiting our role as leaders in the process?

All these quandries focus on how the situation affects us.  To resolve them it may help us to look at it from a different perspective.

A Mile in Their Shoes

What if we were the older, more experienced, technically proficient person on the team – how would we feel?

We have hard-won experience that we hope will be valued.  We have proven skills that we can contribute to the team.  We have settled into a way of doing things that seems to be functional that we don’t want disrupted.

If someone is taking over the team, whoever they are, we probably want those things to be valued.  We want to be valued.  At the same time, we want someone who will set a clear direction and lead us well.

Leading Experienced People - Don't kick over the apple cart.

Will the new leader kick over the apple cart, or will she be more careful as she goes about re-arranging the fruit?

And where will we end up as part of that arrangement?

Dissecting the Dilemmas

Thinking in terms of their perspective makes it easier for us to work through the dilemmas of leading experienced people.

1.  Take charge.  Just because we may be less experienced doesn’t mean we have to be shy and tentative.  If we are in a formal leadership position, we have a job to do; our bosses have expectations of us that we want to deliver on.

Our experienced people have expectations too.  Have you ever been on a team with a leader who failed to give clear direction, coordinate key actions, or wouldn’t make a decision?  It can be really frustrating.

When in charge, take charge. Click To Tweet

2.  Respect the experience. Just because we are the decision-makers doesn’t mean we know everything.  We absolutely don’t.  We’re not the experts.  In front of the group, acknowledge and value the experience of others and talk about the importance of taking advantage of it.

When we meet with our experienced people separately, we should solicit their feedback.  Before making big decisions we should ask for their input.  In doing this, we validate them as team members. In turn, they will be more willing to listen to what we might have to say.

Give them the chance to be heard, and they will be more ready to hear you. Click To Tweet

3.  Cultivate relationships. When we were team members, our job may have required certain technical skills, and we focused on developing those skills in order to be successful.  As leaders, now our job is to focus on relationships, particularly with the more experienced people on the team.

We have to be intentional, make time to get to know them personally as well as professionally.  Our goal is to understand where their skills and experience lie, and importantly, what motivates them.

A specialist knows what to do; a leader knows who to call. Click To Tweet

4.  Put their knowledge to work.  As we understand how they can best contribute, it’s a good idea to put those skills to work as quickly as we can.  In tapping that resource, we are telling them we recognize and value their ability, while at the same time underscoring the character of the relationship between us.

It may be something as simple as asking them to share tips or best practices at meetings, mentoring a new hire to show them the ropes, or tackling a challenging task.

5.  Start with trust.  Teams thrive in environments where mutual trust is high.  Leaders create that environment by being the first to trust.  When asking them to do something, express confidence in their ability, agree on reasonable follow-ups and updates so you stay informed, and resist the temptation to meddle.  Instead, let them impress you with their ability.

Reinforce that trust by being trustworthy.  Only say something if you mean it, follow through on any promise, no matter how small, and be consistent.

Give them the opportunity to impress you. Click To Tweet

6.  Invest in their success.  Some experienced workers may feel threatened by our stepping into a leadership role.  We can defuse their impulse to compete with us or resist our efforts to lead by doing our best to help them shine.

Look for opportunities to give them public credit for work well-done.  Delegate tasks to them that will grow their skills and give them visibility.  Find out what they hope to achieve, and help them take the next step.

We prove ourselves as leaders by helping others shine as teammates. Click To Tweet

7.  Lead them by asking questions. Shouting orders as a leadership technique may work in Hollywood, but most of the time won’t get us very far with real people, especially experienced ones.  Who likes to be shouted at?  Instead, ask smart questions.

  • As we start to set goals, we can ask them what is achievable. “What do you think a good target for this is?”
  • As we reconsider policies and new initiatives, we can solicit their input.  “How do you think we can approach this challenge?”
  • Before key decisions, we can consult them and ask for their thoughts.  “What would be the smart approach from your perspective?”
  • We can even ask how they prefer to be led; that conversation alone can help clear the lines of communication and smooth our working relationships.

In asking, we open the door to clear communication, we demonstrate that we value what they know, and even if we don’t always follow their advice, we’re telling them that they matter.

Leading Experienced People – The Takeaway

In the end, I don’t think these apparent contradictions are actually dilemmas at all.  It’s not a case of either-or.  It’s more about doing the unexpected:

If we focus first on getting feedback from our experienced people, we make it easier to give them feedback.

If we start by granting a measure of autonomy to our experienced people, they will be more willing to align with the structure we build.

And if we focus on helping them shine as positive, productive teammates, we gain experienced allies that will make the whole team more productive.

And that is how we prove ourselves.

Lead on!

Photo credit:  Quino Al on Unsplash

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2 thoughts on “Leading Experienced People: How to Overcome 3 Dilemmas That Make it Hard”

  1. Douglas Mitchell

    Great stuff. This is a situation I have seen mishandled more often than not, and the consequences of mishandling it are severe.

    1. Thanks, Doug – Once we start closing doors to positive relationships we can have with our experienced people, it can be difficult to recover…starting with an open mind, asking good questions, and presenting willing ears can make all the difference.

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