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Getting the Most out of Your Relationship with Your Boss

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How to Turn Your Boss into Your #1 Fan and Advance Your Sales Career


The standing joke in Denver, Colorado, is if you don’t like the weather, wait a few hours.

Sometimes sales reps feel the same way about their bosses.

The truth is, sometimes you’ll get a great boss, and sometimes you’ll get Mr. Hyde. But no matter your opinion of your boss, you’ll need to move the relationship forward if you want to advance your career.  

Let’s start by outlining the pure power your sales manager has to make life a little easier for you:  
    • Recommends you for a raise and promotion 
    • Distributes a bluebird to someone who can handle it—YOU, of course 
    • Becomes a future KEY reference for any future job changes 
    • Approves that two-week European vacation you want to take 
    • Recognizes you publicly and promotes you to the higher-ups

Now let’s look at things a strong leader can choose to do for you:

  • Show you your blind spots 
  • Help you close impossible deals 
  • Advance your current skills 
  • Promote you and give you political shelter 
  • Fight for your commissions 
  • Give you a generous territory 

 Now that we’ve covered the power and influence your boss has over your career, you can see why building a positive relationship is worth the effort.

Eleven Simple Steps to Turn Your Boss Into Your #1 Fan


No one will manage your sales career for you, so if it’s to be, it’s up to you! However, the following steps are practical, actionable, and worth consideration. 

#1. Show your appreciation for your boss’s time, effort, and resources.  

This can be done in several ways. So, here’s an actionable example that demonstrates the point. One salesperson we know would give a shoutout on LinkedIn to their boss. It was a simple visual post that said “Amazing Sales Leader” and read, “Mike, appreciate all you do for our team.”  

#2. Always keep your boss in the loop.

If you lost a deal on Monday, don’t tell them Friday. Let them know ASAP so they are in the know. Share it all, the whole enchilada. Not just the wins, but be quick with disclosing the losses. The longer you wait, the worse it will be.

#3. Make yourself readily available.

Be there for all the meetings and calls—nothing worse than calling someone who never picks up their phone.

One of my clients had someone on the team who never answered the phone. Every time she called, she got the rep’s voicemail. Sometimes this rep would take hours to get back to the manager. This is not the behavior path to promotion –unless you are ALWAYS on your phone closing deals or prospecting, answer your boss’s calls. 

#4. Speak up instead of staying quiet.

Don’t be afraid to have an opinion and voice your concerns or ideas candidly. 

If approached correctly, this can lead to increased responsibility within the organization. Just remember to use good judgment. 

Speaking up doesn’t have to mean complaining. Speaking up can mean here are some problems; here are some ideas to solve them; how can I help? Complaining, as good as it can feel, never does anything until action is taken to resolve the problem.

#5. Work on the relationship.

Always remember that a strong relationship is built step by step. 

And one of the critical underlying foundations of the boss/employee relationship is respect. So, part of your job is to help your boss look good in public. Never forget that. You are like Vidal Sassoon—if your boss doesn’t look good, you don’t look good. 

#6. Stay up-to-date.

Know company news and events, so you can give thoughtful feedback when needed. 

At one of our clients, there was a Sales Leader; we’ll call him Frank. Frank knew everything that was going on at the company. 

He knew when the benefits changed, he knew the comp plan in detail, he knew the marketing team, he knew the CEO’s dog’s name, and he even managed to build a relationship with dull Bob in accounting. 

He talked to other employees, built relationships with everyone on his team, read the company blog, and led the revolution for anti-siloed corporations. When Frank’s boss needed to know something, guess who he called first? When Frank’s boss was promoted, guess who got the job? Frank became invaluable.

#7. Understand your boss’s pet peeves. 

We had a high-level search we were working on and needed to get it right. 

This hiring manager reported to a NEW CEO and needed to make a solid first impression on the new boss. As we interviewed the hiring manager about the new hire profile, we asked about her pet peeves. 

The last thing we wanted to do was put someone in this visible role and have them fail over something “minor.” This would hurt our hiring manager’s reputation and stunt her new relationship with her boss.  

So, we asked her what got her goat. 

And she told us about her pet-pet-peeves. It was not a question we usually asked in our process at the time. But she knew precisely what annoyed her with little thought. And it saved us during the recruiting process. 

We were able to find people with the skills to do the job, but we also found the perfect person who cared about building a solid relationship with her new boss and could avoid the aforementioned pet peeves. 

It became straightforward for our new hire not to irritate her new boss and build a solid working relationship quickly. 

#8. Embrace your boss’s communication style.

 Some bosses want to email; others want to text or jump on a video call. Some will call your cell and expect you to respond quickly. Whatever their preferred method of communication, adapt. It makes you more versatile to work across all communication mediums, so if they prefer a method you hate, learn to adapt. 

#9. Hold yourself accountable and take the initiative.

Building a successful relationship with your boss is essential for both of you. 

Trust will be built by being honest and putting in the effort, and working together will become much more manageable. Finally, beep track your progress to see the fruits of your labor. Keep a spreadsheet of your deals, calls, activities, daily schedule, and whatever you need to stay on target and chip away at your goals.

Don’t Wait Around for Anything

And don’t wait –for anything – take the initiative and start making things happen! 

This way, you will make yourself more visible and win over the hearts of those above you on the corporate ladder.

Sometimes taking the initiative will get you in trouble.

But I say, take calculated risks, and if it’s worth it, do it anyway. For example, in my former life, I started asking around at my huge employer for a list of the TOP 100 Accounts. 

Now, these accounts were worth Mega Millions to my employer. 

But, to me, they were worth nothing because my division wasn’t getting a single dollar from large accounts like these. So my goal was to get the list, find out how to use it, and start making money for my division. 

So, I started asking around. 

I asked and got shut down, and shut down, until one day, my phone rang, and it was the head of another division that owned these accounts. 

I was told to mind my business and that my boss—the President, would be getting a phone call.  

Now at the time, I was mad. 

I was trying to make money for the same company, so I didn’t see why this was a big deal. But my boss didn’t get upset with me. I think he wanted the list, too but felt it would be less intrusive if I asked for it.  

Liberate Your Inner Tiger

So my point is, don’t be the caged tiger. 

Instead, be the tiger who sometimes gets put back in the cage. You’ll get to your goal much faster. And be willing to risk getting in a bit of trouble. It’s better than sitting around waiting for something to happen.  

#1o. Be on time. 

Sounds silly, right? Being “punctual.” 

You probably aren’t if you think you are above this rudimentary tip. Everyone is sometimes NOT punctual. Some people have limited their incomes, career mobility, and reputation by their inability to show up on time. Don’t let that be you. How many deals have you lost by being late?  

One for me comes to mind. 

I moved to a new home and was still finding my way around. I had only lived in the area for a few years, so I was unfamiliar with the layout of the land and had never lived in this area before. 

So, getting in and out was new to me, and I am not directionally gifted, to begin with.  But I scheduled a meeting in an unfamiliar part of the Bay Area and drove to visit the company president about recruiting for an opening.

I got lost on the way there and wound up being an hour and a half late. It took me three hours because I had taken a wrong turn.  

Don’t worry—this was before GPS and Blackberries, so although you may be able to “understand” why I was late, it was nowhere near acceptable.  

Unsurprisingly, I did not get his business. But I did go and apologize. I let him know why I was late, gave him plenty of free strategic advice, and walked out, swearing I’d never let that happen again. This true story embarrasses me to this day.  

Being on time all the time is hard. Don’t lose business over it, and don’t ruffle your boss’s feathers. 

#11. Keep your attitude golden.

I have read research saying your attitude is like your set point. 

Some people are more optimistic than others and are naturally this way. But, for the rest of us, it’s daily maintenance. 

Sometimes all l that’s needed is a nap or a conversation with a trusted colleague, but if you find your attitude going south, you can do things to put yourself back on track. Figure out what works best for you and if you start slipping, use your tools to lighten your mood and put a smile on your face. 

I can promise you that the reps with the best attitudes make more money. 

They get promoted faster, and their bosses favor them. So work on your attitude, and your sales career will skyrocket.    

Getting Ahead Is Nothing New and Requires Patience and Hard Work 

 It’s no secret that building a great relationship with your boss can help you get ahead. 

If you want to accelerate your career path forward and you feel like your current options are limited, get in touch. Reach out to me at [email protected]. 

Together We Can Find Your Next Software Sales Job

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