Career Academy Tool

The Questions that Matter When Starting in a New Role


Life would be so much easier if people just said what they mean.  Why do we find this difficult?  Perhaps we want to keep your options open, keep our cards close to your chest, allow for wriggle room.  Maybe we worry about offending or not “playing the game”.  Sometimes we hope that if we allude but don’t spell out the other party will reach the right conclusion – surely they will take the hint?

Imagine this scenario.  You have secured a much-wanted internal promotion which means transferring to a new part of the business and reporting into a new boss.  It’s an important move for you and you are determined to succeed.  What do you really need to know to ensure this success?   What are you not being told that is likely to have a significant impact on your ability to deliver?  After all, you are probably more than technically competent – the many interviews have proven this – so what is important about the politics, the system, the personalities, the culture of this part of the business that has been left unsaid?  Often at the beginning of a new role we don’t truly know what we are getting ourselves into but trust that the fog will lift and we will find our way through in time without too many bumps.

Several years ago I was beginning a new high profile assignment reporting into a Partner at the Big Four accounting firm in which I worked.  I had not worked with this particular Partner before and so when he invited me into a kick off meeting I approached it with a raft of questions about the client, our deliverables and deadlines  – tasked based subjects that I knew I needed to understand in order to do my job.  Once this Partner had patiently answered my practical questions he suggested we discuss how we would operate together.  I was a bit taken aback  – hadn’t we just covered this?

“This is what you need to know about me” is how the Partner started this part of our conversation.  “What do I need to know about you?” “What might cause problems between us as we start working together?”. “How will we know we are working well together?”.  “What shall we agree now to support each other if things go wrong?”.  “How much do you want to be challenged?”.  “What would be too challenging for you?”. “How will I know when things are getting too challenging?”. “Apart from the obvious measures of success, what is important to you on this assignment?”.

I’ve never had quite the same impactful opening conversation but I’ve tried to emulate aspects of it in my professional relationships ever since.

As a coach many of my clients tell me, in confidence, the questions they want to ask their new (or existing) team member/boss/business partner/colleague but feel they can’t.   I often ask my clients: “If I brought that person in the room and you could ask them anything without repercussion what would you ask?”.  From this there usually follows a conversation about what stops them from asking, what would happen if they never ask, and what could they do or say to find out the answers they seek.

Apart from the questions I was asked all those years ago other questions to consider at the initial stages of a relationship are:

“What would you like me to know about your working style that will help us be effective together?”

“What are the secrets to being seen to be effective in this organisation/team/on this assignment?”

“What will help you trust me as we start to get to know each other?”

“What are the organisational quirks or ways of doing things that I should know about?  How might I inadvertently trip myself up?”

And finally, if you really can’t be up front with these type of questions ask yourself this brilliant question from Nancy Kline’s book “Time to Think”:

“What do you already know that you are going to find out in a year?”

In other words, what is the thing you know deep down about this role/person/team but are choosing to bury for now?  Why is this and what, if anything, might you do about it?