5 Conversations to Have with Your New Boss

This article is the third installment of a three-part series for those starting new jobs.  The first article covered How to Make a Greater Impact in Your Next Job by creating a 90 Day Transition Plan. The second article discussed a simple method to Assess Your New Organization. This third article covers 5 Conversations to Have with Your New Boss to gain clarity in your role and direction.

Have you ever started a new job and wondered what to tackle first?  You received a bunch of information from your new boss, but it seems to lack any coherent direction.

5 Conversations

This article provides insight on 5 critical conversations to have with your boss when starting a new job to clarify your path and avoid unnecessary friction.   The result of these conversations will also provide you with the freedom of movement you desire to gain momentum in your new role.  Having these conversations early will not only prevent unneeded conflict but will set conditions for you to accelerate your success in the organization.

After you’ve started a new job and started following your 90-day transition plan, you will need to have a few conversations with your boss in order to ensure you are on the same page with shared expectations.  The purpose of having these conversations is to ensure you both agree on the direction and manner in which you want to drive the organization that you are now a part of. Having these conversations will help you avoid putting a lot of energy into an idea that either your boss hasn’t bought into or doesn’t agree with.

Ideally, you’ll want to do this after you’ve assessed your organization (first 30 days) and have a firm understanding of the people, processes, and problems.  Having an understanding of your organization provides the context in which your plan will work within.  These conversations are adapted from Michael Watkin’s book The First 90 Days: Critical Success Strategies for New Leaders at All Levels.  The five conversations are:

Your role and situation

As a starting point, line out your understanding of your roles and responsibilities to your boss. Ask whether you see things the same way.  Someone may have already explained this to you on your first day but take the initiative and time to brief back your boss to ensure you have clarity.  This is a great way to save time and future pain by gaining alignment early. If you skip this conversation you risk moving out on great initiatives, but potentially in the wrong direction.  I’ve personally and painfully learned this lesson by skipping this step.

Also, provide your understanding and assessment of the organization in an effort for shared understanding.  Your organization could be a startup that needs energy upfront to get it off the ground. It could be one that is currently successful and just needs minor corrections to sustain that success, needs realignment, or could be a failing enterprise that is in need of a complete turnaround.

Expectations and Goals

Once you and your boss are in synch on your role and the organization’s situation, it’s time to discuss expectations and goals.  It’s a good idea to ask your boss for desired outcomes in the short and long-term. This is a chance for you to shape those expectations by outlining what you think you can achieve over time.  You can have ambitious goals here, but remember it’s always better to under promise and over deliver rather than set yourself up for unmet expectations.

Communication Style

Discuss how your boss wants to communicate in terms of frequency, medium, and what kind of type of content.  Asking your boss “How do you like to receive information?” is a great way to learn how to make your message stick.

Some bosses like to read information in the form of an email or white paper.  Others are visual learners and better understand things through graphs and charts.  You will be doomed to Powerpoint if you are in the military.  Some may like to hear things verbally.  If this is the case, you can help yourself with a little preparation and prepare a narrative to provide the information. Messages are more easily remembered and repeatable in the form of a story.

Resources

You will need resources in some form to get the job done.  This can take the form of money, people, time, training, etc.  This discussion can easily turn into a negotiation. You should be prepared to outline what you think you’ll need to get the job done.  More often than not, you will be asked to get the job done with fewer resources than desired.  This may be due to competing priorities, upcoming deadlines, or merely because fewer resources are available.  Don’t let this become a contentious discussion for either of you.

Understand that you have shared interests here and look for ways to convey mutual benefits in terms of resource usage.  Linking resources to outcomes and providing a menu of options is a great way to gain progress in these discussions.  For example, “With 4 people on the team, I think we can get this done in the next 3 weeks. If we have 3 people on the team, we will likely need another week to get the same results.”

Feedback

After 90 days or so on the job, it will be time to ask for feedback on your performance.  Asking questions about how you are performing and where you have room for improvement is critical for your growth.  Discussing your strengths is just as important to gain better awareness of your unique talents that you bring to the team.  Strengths Finder 2.0 is a great book on this topic.  It is also beneficial to discuss training, projects, or assignments you can undertake to continue your growth as a leader.

 Conclusion

Having these 5 conversations will help save you time and prevent potential friction with your new boss. These conversations will provide you with a level of clarity and direction that will set you up for accelerated success in your organization.

Question: How have you gained clear direction from your boss?

Photo Credit: Marine Corps Gen. Joe Dunford, chairman of the Joint Chiefs of Staff, meets with Adm. Harry Harris Jr., commander of U.S. Pacific Command, at Pacom headquarters at Joint Base Pearl Harbor-Hickam, Hawaii, Feb. 1, 2018. DoD photo by Navy Petty Officer 1st Class Dominique A. Pineiro