Conversations with Your Team, Peers and Boss - New Tech Leader Series

(Note: This post is part of a series for new technical leaders that are joining a new company, or taking over a new organization or team; and while written for new CTOs, VPs of Engineering, or Software Managers, could be applied to other technical positions.  This is also written largely for smaller to mid-size teams with a bend towards startups.)The crazy thing about managers is that the majority of your job is working with people – and unlike software, which is normally pretty deterministic, people can be unpredictable and difficult to understand.Whenever you first join a new team the most important thing you can do is listen and observe.  Get to know the players and the company culture.  Here are some things to get a handle on in your first month:

• How are new ideas presented?  Do people build consensus or just go forward?
• Are meetings efficient?  Could they be improved?
• What happens when things go wrong?  How are issues handled?
• How are new employees on-boarded?  Is there any documentation?

In general I like to get on every email list, and attend every meeting that I can during my first few weeks.  It is a great way to immerse yourself in the way things are currently operating, which gives you the chance to make mental notes of inefficiencies or potential areas for improvement. Plus taking a few weeks to a month of just getting your feet is a great way to make sure that when you do have a change or suggestion, you are able to execute it within the norm of the company.

Meeting with your Team

During your first week or so, make sure you take the time to meet with each of your direct reports, and the other members of your team.  Getting face time with everyone in your organization shows that you care and can help you integrate faster – plus it gives you a great chance to get a full view of the organization and personalities in each pocket (and if you are in startup, then it is likely your team is relatively small so this should definitely be doable in the first few weeks on the job).Your goal in these initial meetings should be to just listen and get to know each person.  This means actively listening and preparing a good list of questions ahead of time.  Here are a few to get you started:

• What is your background and what brought you to <insert company name here>?Learning a little bit about each person will help you understand his or her skills (since people aren’t usually defined by the jobs they have and can be capable of a lot more).
• What do you love most about working here?These are the things you definitely don’t want to change.  So pay attention, if you mess up the things people love most then you could have attrition on your hands.
• Where do you want to take your career over the next 5 years?  What skills are you looking to develop?This is important to know because for top performers it can give you a chance to present opportunities to help them grow and develop.  Plus in any organization you will likely need succession plans so knowing where people want to go can help you make strategic moves that can also win favor with employees.
• What has been your greatest success or accomplishment at <insert company here>?  What made this standout for you over the other work/projects/etc.?Asking this question will help you understand what makes this person tick, and also what work they consider to be important or valuable.  This is a great question to dive into and ask more clarifying questions, like what their role was, how long the project lasted, what happened afterward, etc.
• What are the biggest challenges facing <insert company here>?This is a great question because it helps you understand what each person sees as a potential concern.  Addressing these concerns and giving people visibility into progress against these challenges will inspire and motivate – helping build credibility and early wins.  Also, if these are drastically different in various parts of the team or organization, you can gain valuable insight into potential areas of misalignment.
• If you were in my shoes what would you do first?  What changes would you make and why?Make sure you don’t make any promises to anyone, but understanding what different people want you to do and why can help you identify the some immediate things you can do to add value.  It also helps phrase a negative question in a proactive and positive way – so people become part of a solution instead of complaining to you about things they aren’t happy with in the company.
• Is there anything else you want me to know?You can phrase this lots of different ways, but having a catch all question that opens the floor is great to allow your team members to share their opinions if they have them.  I have found most people don’t have anything to say, but the ones that do appreciate the opportunity.

Once you have had a chance to meet with you direct team members, then next step is to build relationships with other strategic people within, and outside, the organization.

Building Strategic Relationships

First and foremost are your peers, these are your first team (I stole this term from the book 5 dysfunctions of a team – here is a good summary if you aren’t familiar), and represent the people who will be able to help you understand and succeed in your new role.  Building these relationships early is important because these people can give you clues on how to interact with your boss, tips on the previous progress and conduct of the team, and can be great resources if you have questions or problems.You can adapt some of the questions from above, but here are a few more to consider as well:

• What has made your successful at <insert company name here>?
• Do you have any suggestions or do’s/don't’s for working with our manager?
• What is your impression of the company culture?  My team culture?
• What are the biggest challenges on my team? 
• Are there any personalities or team dynamics of which I should be aware?
• What do you think is the most important thing for me to focus on?
• What are the biggest challenges facing our industry?
• What is your impression of the competition? Is there anything we should be concerned about?
• Any other advice or suggestions?

Again, this is a conversation, listen to their answers and take notes if you need to do so.  And afterward, make sure you take the time to say thank you.  Send a personal note or a card, there is no doubt that these people are very busy and showing gratitude for their thoughts and advice matters and will help you build an ongoing relationship with them in the future.Besides your peers, it can also be important to meet with external vendors or strategic customers.  This is a great way to get an outside view of the company and leadership, and give you a chance to make these relationships stronger and potentially better (in the event they are tenuous).  Again, treat these people with the utmost respect, just like you would your boss.  Prepare ahead, listen thoughtfully, take notes, and follow up with a thank you (or actions on the relevant tasks or items that may have come up).

Meeting with YOUR Manager

In addition to meeting with everyone it is also important that you take the time to meet with your new boss as soon as you can (I would recommend the first day or two on the job if possible – and schedule this in advance if you can, that way you know you will have the time set aside).  The main goals of this meeting (or potentially subsequent meetings since there is a lot of information to cover) are to understand the expectations for your role, setup a rhythm for communication, and to also provide your plan of action.

Understanding Expectations

It is important to get a feel of what is expected of you and your new role.  This includes getting a feel for how your manager perceives the performance of your team in the past and present.Here are some great questions to ask to help narrow in on what matters:

• What is the more important thing for me to focus on now?
• What does success look like in 6 months?  12 months?
• What are the biggest challenges facing the company, and what is my role in addressing them?
• How do you define the company culture?  Do you think employees agree?  Why or why not?
• What was the previous <insert your position here> great at?  Were there areas that could have been better?
• Is there a hiring or operating plan?  Does it need to be updated or modified?
• What are the key company metrics?  How does my team impact them?  How do you measure success?
• What decisions do you want to be consulted on?  What needs your approval?
• Are there any top performers on my team?  Who are they and what is their history?
• Are there any poor performers?  How long has this been the case and what has been done to date?  Are they recoverable or should they be terminated?
• Are the right people in the right roles in the organization?

Setting Up a Rhythm

Besides getting a handle on expectations, it is also important to understand how your new boss likes to operate.   This way you can be sure to setup the right framework in advance and communicate in the right medium at the right frequency.

• How should I communicate status?
• Do you prefer email or verbal communication?
• What regular meetings should take place and how often (i.e. 1:1s, all company meetings)?
• How are performance reviews conducted (if at all)?  What about goal setting for employees?
• What is my budget?  How should I go about financial decisions?  How much do you want to be involved?

Your Action Plan

One of the best pieces of advice I received was that you should set your manager’s expectation that you have a plan and that he (or she) can expect results in 90 days.  That gives you enough to get familiarized with the organization and goals that you can feel confident in your decisions.  Setting this expectation from the get go allows you to push back in the event that your boss is pushing you to action before you are ready.Another key thing to contribute is how you plan to communicate progress and what deliverables you plan to produce in your first months on the job.  One easy one is the technical risk assessment I mention in another post, but it can also include things like an organizational review, operating plan, or even specific project deliverables.  Establishing this up front, and then delivering on those promises will secure early wins and give your manager additional confidence in you meeting your other planned objectives.---Of course this doesn’t cover everything, but should be a pretty good guide to get you started on some of the crucial conversations you need to have in your first days.  And if you have other ideas, or links, don’t hesitate to post them in the comments.