8 Signs Your Boss Wants You to Stay

by Pranav Ramesh
January 29, 2021

Every employer wants a highly-engaged team that is truly bought-in to the task at hand. Building that team is difficult enough, retaining it can be tougher. One of the most difficult, and crucial challenges your boss faces is holding on to people like you, their top performers. Here are 8 signs that your boss wants you to stay a part of their team for good.

Topics Covered:

  • They Ask for Your Opinion
  • They Are Honest and Direct with You
  • They Are Understanding
  • They Keep Open Lines of Communication
  • They Give You More Responsibility
  • They Give You Regular Pay Bumps, Perks, and Promotions
  • They Invest in Your Growth and Training
  • They Ask You to Train Your Peers

They Ask for Your Opinion

No one has all the answers, not even your boss. Great leaders know how important it is to seek out thoughts, ideas, and opinions from every trusted source, no matter who that is. If your boss truly wants you to keep your current position, they’ll seek out yours.

They Are Honest and Direct with You

If your boss is happy with your work, they will usually be more candid with you. Often, this means they are thanking and commending you on a job well done, but that’s not always the case. When your boss is more comfortable with you, they tend not to hide their feelings, good or bad. If your boss is giving you constructive criticism, it means they believe in you and want you to excel. Take that as a sure sign that they want you to stay.

They Are Understanding

Let’s face it, life happens and no one is perfect. We can’t always control what happens to us and, even when we can, we sometimes make mistakes. Leaders understand this, they have made plenty themselves, and they tend to know the difference between reason and an excuse. When something bad happens, preventable or not, your leader will seek first to understand and to help if they really want you to stay.

They Keep Open Lines of Communication

Your boss is a busy person. Client calls, team meetings, and a string of endless responsibilities eat away at their availability. Chances are, it can be tough to connect with your boss as often as you may like. But if they really value you as an employee, and want you to stay, they will keep lines of communication open when you truly need them.

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They Give You More Responsibility

When your boss trusts and values you, they are more likely to give you more to do. They’re not just passing along more work, though, they are following a strategy. Leaders understand that responsibility helps create ownership, buy-in, and overall engagement within employees. Considering the fact that unengaged and actively disengaged employees are 65% more likely to leave, your boss has a strong incentive to keep you interested.

They Give You Regular Pay Bumps, Perks, and Promotions

It may seem obvious but is worth noting, that consistently incentivizing you is a strong sign your boss wants you to stay. Your company likely has an annual review program with pay increases attached. Most people today expect to make at least a little bit more each year than the year prior. More often than not, these increases are based on a scale, meaning your boss has some choice over how much it is. If they really want to keep you around, they’ll make a point of letting you know they did what they could to get you as much as possible.

They Invest in Your Growth and Training

Humans are constantly evolving. From a professional standpoint, evolving means learning new skills, enhancing your current ones, and working on your personal development. When your boss wants and expects you to be in it for the long-haul, they will spend the time and/or money required to help you do just that.

They Ask You to Train Your Peers

Every new hire needs to be onboarded the right way. Though your company likely has a formal training program, the learning hardly stops there. Your team leader often wants to partner the new employee, or even your peers, with someone they trust to “show them the ropes”. If that person is you, it’s time to celebrate, because that means they trust you. Your boss is subtly telling you they want this person to be like you which is a strong sign they want you to stay a part of the team.


Your boss is busy; they are handling client calls, dealing with complex issues, and strategizing for the future. They don’t always have time, nor should they, to handle every situation that arises. If they’re a strong leader, though, they will recognize how important it is to hold on to their best employees. If your boss is giving you these signs, odds are good that they value you and want to keep you on board.

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About the Company:

Peterson Technology Partners (PTP) has been Chicago’s premier Information Technology (IT) staffing, consulting, and recruiting firm for over 22+ years. Named after Chicago’s historic Peterson Avenue, PTP has built its reputation by developing lasting relationships, leading digital transformation, and inspiring technical innovation throughout Chicagoland.

Based in Park Ridge, IL, PTP’s 250+ employees have a narrow focus on a single market (Chicago) and expertise in 4 innovative technical areas;

  • Cybersecurity
  • Artificial Intelligence
  • Data Science
  • Cloud & DevOps

PTP exists to ensure that all of our partners (clients and candidates alike) make the best hiring and career decisions.

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