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Start-up Conversation Guide

Do you have a new team member? A quick conversation about how you each like to work can kick-start results and save a lot of problems down the line.

Do you have a new team member? A quick conversation about how you each like to work can kick-start results and save a lot of problems down the line.

Why does a start-up conversation matter?

All managers have a preferred way of working. You only have to think about your own experiences to know that each boss has their own expectations and idiosyncrasies. Whether you’re setting up a new working relationship or need to reboot and existing one, the faster your people know what you need, the faster they can adjust.

On the flip side, employees need you to understand their needs. As Carla A. Harris, vice chairman at Morgan Stanley, put it, “Gone are the days when you can survive as a my-way-or-the-highway type leader.” Instead, your team member will be looking to you to help them deliver their best work by adapting to their preferences, not treat them as a box on an organizational chart.

To guide the conversation, there are three key aspects to explore, best framed as questions:

Q1: What day-to-day approach will work best?

The first step is to talk through those crucial but often-overlooked dynamics that form the backbone of your working relationship. These include:

  • How you each see your responsibility to the other
  • What great collaboration looks like
  • How often you’ll catch up together
  • How hybrid working will operate
  • What team ‘norms’ are important to know about
  • How feedback will be collected
  • How compensation works

Q2. What impact do our personal values have at work?

The second area to cover is what makes you and your team member tick. These are not your organization’s values, but the two or three principles or beliefs that are most important to you both personally at work. Values may seem like an airy topic to discuss, but the reality is they influence our behavior in almost every way, including our choice of goals, how we make decisions, and how we respond to the actions of others. Even our “to do” lists reflect our values in some way, since they’re as much about what we choose to do as about what’s necessary. For example, if you had to pick two values from the list below, which ones jump out? More importantly, how do these affect your approach at work?

Examples of values

The same applies to your team member. Do they put special emphasis, for example, on one of the above, or perhaps giving something back to society, having variety, or being the best? Each has a vastly different implication for what they’re looking for in their work, and therefore what they need from you. Whatever their top values are, talking them through can help you to get the best out of your team member.

Examples of Values

Q3. What important boundaries are there?

Chris Hadfield, former commander of the International Space Station, commented: “No astronaut launches into space with their fingers crossed.” It’s a principle that applies just as much when moving to a new working relationship, or any venture into the unknown. Risks can be reduced significantly by being clear-eyed about what’s OK and what’s not OK, and then communicating this to your team member.

If discussing boundaries seems heavy-handed just when you’re trying to enthuse your team member, keep in mind that, counter-intuitively, the problem cuts the other way. Without boundaries, people can be left feeling anxious about making mistakes. Understanding where they can operate safely and where to go no further will create a much greater sense of freedom. There are significant advantages for you, too, including fewer sleepless nights just for starters. Typical boundary areas that are useful to discuss, for example, may be specific deadlines, decision-making limits, or budget constraints. Even simple non-negotiables such as being available at certain times of the day or dropping you an email when a key task has been completed can be helpful.

Your team member will probably also have one or two boundaries you’ll need to know about. Family responsibilities such as collecting kids from school, work-from-home opportunities, and expectations about their role are often top of the list. Overstepping what they see as a clear line in the sand can often be a deal breaker, but unless you know what this is, it can be all too easy to make mistakes.

A final thought

It takes a bit of extra time to have this start-up conversation, but it’s more than just a re-set. By jointly exploring needs, it’s an opportunity to set the tone and approach for every discussion you’ll have together from now on, one that acknowledges that both sides have a responsibility to make it the best working relationship possible. Great for your team member, and great for you, too.


Start-Up Conversation Guide for managers
Start-Up Conversation Guide for team members
For more help see Now You’re Talking!
The manager’s complete handbook to leading great conversations at work – even the tough ones
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