Working With Senior Leaders

If you’ve just entered a new position that requires you to interact with senior leaders, it’s normal to feel intimidated. Maybe you’ve only ever worked with junior employees and middle management — how are you supposed to behave around people with such power and experience? What if you make an error that jeopardizes your relationship with or access to an important contact? You may even be concerned about damaging your career.

Working with senior leaders is like working with anyone else, except that they have a stronger influence over the trajectory of your project or career. While this is something to consider in your interactions with executives and experienced leaders, it should not change your character or fundamental approach. The most important things are to be strategic and well-prepared in formal interactions and intentional, respectful, and authentic in your informal interactions.

Formal Interaction

Formal arenas like meetings and pitches have certain rules of engagement. Sure we’ve seen people in films who are able to wow a boardroom full of executives with their off-the-cuff genius, but the safer and more realistic bet is to be extremely well-prepared.

Be Brief

Regardless of your relationship with an executive outside of your pitch or meeting, assume that when they are in work-mode, they have a packed schedule and little time to discuss and ruminate before making high-stakes decisions. They will not want to sit for a long presentation, no matter how well you’ve laid it out.

Get to the point

When you are pitching to an executive or senior manager it is important to distinguish between how you would present your idea to the general public versus a seasoned industry veteran. Senior managers will be used to the tools used by public speakers to engage an audience, and will likely be more interested in facts and figures, so get to the point directly.

This doesn’t mean your presentation has to be bland or lacking a compelling narrative — just imagine that you’ve promised a 30-minute audience with the executives of your company and the day before the meeting your time is cut down to 5 minutes. What are the most relevant pieces of information to include?

The optimal layout of your pitch should include:

1. The problem you are trying to solve

2. Your solution

3. Your business model including return on investment

4. Plenty of time for questions

Make sure that you stick to your agreed-upon agenda

If they are there to hear you pitch about X, don’t pivot the night before and decide you’re going to talk about Y.

It is also vitally important that you be prepared to answer whatever questions they might throw your way.

Rehearse before presenting with several different colleagues and encourage them to throw their hardest questions at you. Make sure that you’re comfortable with supporting any figures you’ve included in your presentation and if you can’t answer a question, acknowledge that and promise to follow up when you have an answer.

Keeping your presentations tight and to the point will show respect for their time and will indicate your professionalism and preparedness to work amongst them.

Informal interactions

If you have the opportunity to interact in informal environments with senior leaders, you have a unique opportunity to develop relationships with people who could positively impact your career or project. Do not let the pressure of this opportunity get to you. You want to establish a peer dynamic with these leaders, and acting star-struck or out of your depth will undermine that.

Project your worth and value

Establishing a peer dynamic does not require you to adopt an arrogant persona or to feign knowledge of topics you know nothing about. It is about confidently projecting your worth and value to convince these leaders that you belong in their circle.

Find common ground to discuss

You can achieve this by connecting on a business level—doing your research to have a stance on work that they or their company is doing. Sharing insights about your own learning in your business development that you can find common ground to discuss. Share ideas about popular issues in the world of business and also industries that you see as ones to watch.

Where appropriate, look for opportunities to connect more personally

For this one you’ll need to assess your dynamic to see if this is appropriate, but in many cases it will be. If you feel comfortable, talk about your family, hobbies, and interests outside of business. You may be surprised by the overlap you find, even with people a generation older than you.

Finally, don’t let an awkward conversation or silly mistake discourage you from trying again. As trite as it sounds, learning is about making mistakes. If you stop trying after your first embarrassing encounter, you will not get far.

While it is important to treat senior leaders and executives with respect, it’s also important to remember that they are human beings. Don’t rush to put them on a pedestal because of their job title or salary — try to find common ground.

Keep growing,


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