What Nobody Tells You About Working With A New Boss

When I was in consulting where I frequently had to meet new clients, building trust with them quickly was part of the job. I wanted to make a good impression, so I would go straight into establishing credibility by coming up with lists, reports, and reminders for them.

Yet, a lot of times I found myself repeating information when they asked the same questions about things I had already provided. It was very frustrating.

Then it dawned on me. I was so focused on what I wanted. My list. What I thought would work. 

What about what they wanted?

That changed everything.

1. Use the first conversation to build the relationship

With a new leader especially, take time to build the relationship first.

I learnt this the hard way. Walking into a first meeting with an agenda full of updates and asks felt efficient to me. To them, it felt transactional, because we had not built any trust yet, and I was making huge asks. 

That first interaction is also  not the time to talk about promotions or your career development plans. Those conversations matter, but they need a foundation of trust to land well.

Instead, use that first conversation to learn about them. Understand their expectations and how you’re going to set your relationship up for success.  

If you want to go deeper on this, The Trusted Advisor by David Maister is one of the best books I have ever read on building trusted relationships - it was a holy grail in my consulting days! 

2. Align on how they want to work

Once I stopped leading with my agenda, I found myself being more curious and started asking better questions.

Before you start managing up, you need to know what managing up looks like for this specific person. Here are the three questions I always ask early on:

What is your preferred way of communication?

Everyone has a preferred communication style and our job is to understand which works best for them. Give them options rather than leaving it open. You want to avoid getting a vague "just message me whenever." Prompt them with specifics. Is it WhatsApp for anything before 8pm, Slack, weekly meeting reports, or one-on-one sessions with summary notes twice a week?

How regularly do you want to be updated, and how?

Again, give them something to react to. For example, do they want a quick email every Monday morning, or thirty-minute syncs before bi-weekly leadership meetings?

How do you prefer feedback and escalations to be shared?

Real time or scheduled? And importantly: what would they consider a red flag that needs to be brought to them immediately?

These questions show that you are thinking about their needs, and what alignment looks like in practice.

3. Link the relationship to your development  only when the time is right

After I had built that foundation, the career conversations became so much easier. My leaders were invested in me because I had invested in understanding them first. Think of it like your savings account, we withdraw from it only when we’ve saved up enough!

Once you have established rapport and trust, then you can begin to plant a seed about your development.

It can be something like:

"I would love to share my career development plan with you and get your thoughts. I would also love to build it together with you. Should I work directly with your EA to book some time? I am happy to share what I have reflected on ahead of time for context, if that would be helpful."

This signals that you are proactive, that you are thinking ahead, and that you want to co-create your growth with them. That is a very different conversation from asking about a promotion at the first meeting.

The goal of managing up is always to align. When your boss understands how you work, and you understand how they work, everything else becomes easier.

Rooting for you,
Angel Kilian
Founder | Career inFocus