6 Tips for Conversing with Someone More Seasoned Than You

HR insights and tips with Jeff Havens

Hello, and welcome to another installment of HR Intervention! This one is for anybody who’s currently stuck working with a bunch of old people.

Not that you have a problem with old people — far from it! You know plenty of delightful old people, and your grandparents have been buying your love for years with that check they send every birthday.

But issues arise with your colleagues when they act old, playing it waaaay too safe. They wouldn’t know a brilliant new idea if it smacked them in the face, and trying to convince them to make changes is driving you nuts!

Unfortunately, you’re going to be stuck with them for a while, and with all the recent advances in medicine, they just might be working right next to you for forever.

You’re welcome to try avoiding these people for the rest of your career. You can complain to your friends about their stodgy ways and shake your head at their stubborn refusal to acknowledge your genius. That’s certainly your right.

But if you want to earn real respect, here is a step-by-step process to help you bridge the gap between you and anyone significantly older or more experienced than you are:

1. Expect Some Condescension 

Nine times out of ten, it won’t be intentional. Yes, you’ll run across the occasional know-it-all, but you can find those people at every age.

For the vast majority of your older colleagues, however, they simply like the way they do things because they’ve found success with those strategies, and they’re not immediately going to see any need to do anything differently. Neither would you in their position.

If you interpret their attitude as an attack on you and your ideas, you’ll be setting yourself up for a fight. If, instead, you realize that they don’t mean to make you feel inferior or unappreciated, you’ll be prepared to establish a strong relationship.

2. Let Them Do Most Of The Talking

At least at first. Your turn will come. Unless you’ve been hired because of your particular expertise, then you have to accept your role as the student.

If you’re willing to listen, most of your older colleagues will be happy to talk about what they do and why they do it that way, partially to initiate you into your company’s culture and partially because all of us like talking about things we understand very well.

Establishing yourself as a willing listener is a critical element of any successful relationship, and there will be plenty of time for the inevitable questions and ideas you’ll be stockpiling while you learn how things currently function.

3. Praise Anything You Hear That Sounds Intelligent

If you’ve ever tried teaching a child to play the piano, then you’ll know how frustrating it is to go through a painstaking explanation of chords and scales and melodies, only to watch the child ignore everything you’ve said and play whack-a-mole with the keys.

In exactly the same way, your older colleagues will be equally frustrated if you listen to their explanations about how and why they do things, only to start in with your own new and better approach.

If you can’t find something reasonable, intelligent, shrewd, or eye-opening in the way your company currently operates, then you either haven’t been paying attention or you’ve been hired into the wrong company.

The second you let your older colleagues know that you value what they’ve done, they’ll be better prepared to listen to you. Just don’t take this one too far, or you might come off like a brainless brown-noser.

4. Ask A Lot of Questions

If you understand the way your business works and have some ideas about how to improve it, there are basically two ways to go about it.

Starting out with “I have an idea,” implies that you’ve come up with a foolproof solution to the wealth of inefficiencies your older colleagues are too blind to see, and it will probably make them slightly defensive.

Instead, try something like, “Why are we still advertising on mainstream radio?” or “Has anyone ever conducted a focus group with Latin American families?” This way, you can introduce your ideas under the guise of trying to more fully understand how things work. It feels slower, but it will work better — and more quickly — than trying to start at the finish line.

5. Expect Some Frustration

When you ask a ton of questions, you’ll probably get some pushback. If your older colleagues are comfortable with the way they do things, they won’t enjoy the implication that there’s something wrong with it. And neither would you, so don’t expect them to be happy with all of your suggestions.

The process of consciously incorporating new ideas into our existing framework is always a bumpy one, and this will be no different. If you get mad at them for not immediately embracing the wisdom of whatever it is you’re saying, you’ll accomplish nothing.

6. Focus On Improving The Business 

Now you can act. You’ve positioned yourself as attentive, thoughtful, and appreciative of many of your older colleagues’ ideas, but you’ve also asked enough questions that it’s clear you have some ideas of your own.

If your 55-year old team lead is dead set on ignoring everything you have to say, take your ego out of it. It’s not that it’s your idea; it’s that the idea could save money, eliminate redundancy, or reduce stress.

If you’ve asked questions your older colleagues didn’t know how to answer, point out that their inability to do so is basically the same as admitting that there is a problem — or an opportunity.

If they still don’t listen, find a different older colleague and repeat the entire process until you get one of them on board. Everything is easier with allies. Is it fun when more experienced colleagues choose not to listen to those with less experience?  No, but don’t worry. Your ideas will have their day.

Talking with someone much more seasoned than you doesn’t have to be difficult. It just becomes difficult sometimes because we want things to happen faster than they are likely to.

Trust me, I also wish you could start the New York Marathon at mile 25. But I’ve tried, and the police are just not accommodating to that idea.

Learn more strategies for helping different generations work cohesively, in this free webinar with Jeff Havens:

Jeff Havens is a speaker, author, and professional development expert who tackles leadership, generational, and professional development issues with an exceptional blend of content and entertainment. He is a contributing writer to Fast Company, Entrepreneur, BusinessWeek, The Wall Street Journal; and has been featured on CNBC and Fox Business. For more information, or to bring Jeff to your next meeting, call 309-808-0884, email, or visit


Speaker, Author and Professional Development Expert