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Make Your Boss a Best Friend

Updated: Jul 19, 2023

by Stephanie Bickel

leadership communication skills

The relationship you create, develop, and strengthen is crucial for a meaningful and impactful work environment for you both. It's important that you have open communication, transparency, and establish a relationship built on trust.

Here are 5 Best Practices to Make Your Boss a Best Friend:

1. Balance personal and business relationship

Your boss can be a personal relationship. Give yourself permission to share personal pressures and personal dreams. Share how working with this boss is making you a better brother/sister, son/daughter, father/mother, spouse.

2. Promote your boss through all channels

Do this through social, peers, cross-functionally, and to leadership. Think omni channel. Do not wait to be asked. Initiate sharing positive praise about your boss to others in your organization and to clients and customers. Quote your boss to others. Tell people what your boss has taught you.

3. Listen to your boss’s dreams

You are on a treasure hunt to find out exactly what your boss is hoping and dreaming of. Some will tell and others will not be honest even with themselves on this. See what you can interpret in the unsaid. For example, your boss says she cares about growing the team and the bottom line, but you see her spending a lot of time working on a special side project. That is an incongruency. Maybe the truth is that she wants you to grow the team and revenue, while she focuses on a different goal. Pursue what is really most important to your boss and then clarify it for the boss to make it even more attainable.

4. Deliver pep talks – encourage your boss

Check out our 5-step framework to delivering a great pep talk. Your boss is likely exhausted trying to protect morale and motivation for everyone else. Be the one person your boss can count on for a pep talk. Get good at giving them. Get great at timing them. When should you give one:

  • After a tough meeting

  • After a rough email exchange

  • After an unexpected obstacle emerges (budgets are cut, a star employee gives notice)

  • After something hard happens at home

5. Get them more free time – take work off their plate

Tell them they can come late to a meeting and you will run the opening. Release them early from meetings when they are not needed. Look ahead in their schedule and offer to handle a meeting without them on a crowded day. Offer to write email drafts. On group email chains, be the first to respond with a thank you to save your boss the energy/time of that. Offer to attend meetings and just take the notes for follow-up. Offer to review recordings of a key meeting and write the proposal.

When I ask the happiest and most successful leaders about their best friends, they always talk about a boss or a direct report that they still keep up with in retirement. Put a long lens on these relationships. No one knows you like a boss does. It's a special special relationship.


Great leaders and speakers start with Speak by Design. Learn the techniques and build the skills with us. Speak by Design University is the only leadership communication program in the world that gives you access to self-paced learning, group coaching and training and, most importantly, private one-on-one coaching. Learn more and register.


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