Help your boss succeed

The purpose of this blog is to highlight some of the techniques to ensure your new boss is on your side.

Don’t be a wall flower

Your boss will have more impact on your results, successes or failures than anyone else in the new firm or in your new role. Therefore, you need your boss’ support for your 90-day plan and to avoid getting sucked in immediately to fire fighting. It’s 100% your responsibility to make the relationship between you and your boss work. One technique is to stay engaged with your boss daily, minimally weekly.  Remember, in a new persons’ position, no news is bad news.

Nobody likes bad news.  Bringing bad news to the boss is risky, but if you’re the one who discovered the issue, I believe is you’ll catch more flak by not divulging the discovery early enough.  This may be your early win.

However, don’t solely approach the boss solely with bad news.  If/when you must present bad news, accompany the news with resolution options.  You’re certainly discovering positive aspects of (e.g.) the business; report on this also.

Help your boss succeed

Some early wins should be based solely on your boss’s priorities and by now you know what his or her’s top pain points are.  You want to stay focused on the top 3 and provide exception-type weekly updates on what you’re doing about them.

The five essential conversations

I’ve learned that there should be five important conversations with your new boss.  They need not take place in isolation of one another, but interlaced.  There is however a logical sequence to the conversations (these also make excellent interview questions):

1. State of the nation: A conversation on how he/she views the organization with a goal of arriving at a situational agreement.  Reaching a shared understanding of the situation(s), its challenges and opportunities is essential.  This will become the foundation for everything you will now do. Regularly confirm and clarify the situation and objectives and don’t let key issues remain ambiguous or misunderstood between you two.  Importantly, a tie in a misunderstanding goes to your boss, not you.

Even though your boss will not likely be aware of the STaRS model, determine which STaRS mode the business, major processes or products are in.  Additionally, learn what those who preceded you have succeeded in, or failed in, and how.

2. Expectations: You need to seek, clarify and negotiate expectations. Learn what is required from you in the short and medium term and the associated success criteria.

3. Interface: Determine how you and your boss will engage going-forward and how often.  Will you engage face-to-face or on Facebook?  What decisions can you make, what kinds require his/her consultation or approval, and when can you take over decisions temporarily being performed by your boss?

4. Resources: Determine what resources are available to you (i.e. funding and personnel).  What do you need to be successful?

5. It’s all about me: How will your term in this role enhance your personal development and what areas will need improvement?  Are their courses that would help you in your new role?  Show a willingness to seek candid feedback to where personal development is needed.  However, as many are uncomfortable in expressing blunt feedback, use a tool like to obtain anonymous feedback from peers, direct reports and your new boss.

You’ll also want to have these five conversations with your new direct reports, but not right away as you need to focus on you first.

Help me to help you

The list below illustrates the different ways your boss can positively impact you, or in other words, your boss’ role in transition.


  • Help getting needed resources quickly
  • Establish clear measurable goals
  • Provide guidance at strategic break points
  • Help staying focused

Turnaround, same as Start-up plus:

  • Provide support for making and implementing tough personnel calls
  • Help cutting deeply enough and early enough
  • Provide support for changing or correcting the external image of the org and its people

Realignment, same as Start-up plus:

  • Help making the case for change

Sustaining success

  • Constant reality testing
  • Support for playing good defense and avoiding mistakes that damage the business
  • Help finding ways to take the business to a new level

While you may have stylistic differences between your boss, your goal is to get measured on results.  You may also not share thanksgiving dinner with your new boss, but it’s essential that your professional capabilities be respected.  If they’re not, your days are numbered.

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