Six questions senior leaders wish you would ask in your one-to-ones

one to one

A one-to-one is a chance to review, reflect and create actionable next steps for your career — but it can also reveal a lot about your ambitions and outlook along the way. We asked six senior leaders what they wish you would really ask them when you meet — and why…


Lisa Ruch, Director of Business Development, Chemonics

‘Can I offer you some feedback?’

This is a question I wish that my direct reports would ask me — and one that currently no one asks me. I’d love to have that kind of open dialogue around how we could all be doing better. I think there’s a sense that leaders have to know everything and we’re infallible, which of course is not the case. Often, I feel like I’m flying a bit blind and operating in a feedback vacuum where I don’t really have a sense of how I’m doing and whether the way that I’m managing the team is working for everyone. If someone were to ask me this question it would tell me that they have thought through what they would like to see that would be different and how things could be better for the whole team. For someone to bring up this question though you do have to have a business culture where feedback is not seen as threatening and is given and shared fluidly. Our former CEO once said that she always thought of feedback as showing that you cared about someone’s performance and about their future. And if you’re offering feedback to someone in a leadership position it usually means you care about the broader organisation.

Dr Michelle Goddard, Data Protection Officer, Financial Ombudsman Service

How can I bring more value?

For me, one-to-ones are an opportunity for broader thinking, so I want the question from my direct reports not just to be how can I be better, but how can I maximise my value and in turn how can I maximise value to our clients? That speaks to strategy — and what that tells me is that you’re not just looking at your own direct narrow silo-ed objectives, but more broadly in terms of the organisation. Business needs people now who are going to be able to collaborate and you need to be able to anticipate and understand that the expertise isn’t all within you alone. So, as a leader you’re looking for someone who’s prepared to interrogate issues across the piece. Working for an independent public body is very much about fairness and consumers, and although sometimes it can be hard to see a direct thread within the work that we do, I always want people to be going back to the mission of the organisation. And that’s what that question tells me they are doing, in terms of delivering outcomes for consumers and making sure we’re driving towards that.


Samantha Eardley, Marketing Director and UK Schools Sales Director, Collins

‘What does this development mean for us and how can I impact positively on that in my role?’

It’s often a challenge for junior members of the team to relate what they hear in a monthly town hall or update to what they’re doing day-to-day. So, I really like it when someone picks up on a dynamic that’s going on in the market or something a competitor has done and asks about it to demonstrate that they’re thinking one step ahead. That shows they’re looking at the point of what they’re doing and the bigger picture, and that’s important particularly in marketing, when it can be quite easy for team members to fall into a situation where they’re just thinking about delivering the campaign that’s in front of them. You need confidence to be able to ask this question and it’s nice when people do start having those conversations, because you think, ‘Okay, they now feel happy to do that’. When people start making those connections it also shows you that’s somebody who’s really going to excel in their role. It’s probably one of the things that would make me think, ‘This person is ready to progress’. Or, ‘I can see how this person could be moving into a managerial or more strategic role in a few years’.

Kim Pasche, Senior Director, Global Virtual Sales EMEAR, Cisco

‘Can I get some help with this?’

The world, 20 months on from the start of the pandemic, is looking for people to portray much more empathy than in the past. A powerful question for me would involve something around vulnerability in themselves or perhaps asking for help with something or with their team, such as how they could best approach the issue of everyone going back to work in the office. We will all have to figure out how to remain inclusive in the cultures of our teams through the hybrid transition and one of the biggest challenges any company is going to have is how they approach this. There will be people who don’t want to come in and those who do, and managers who can show empathy and do not want to push all their employees to go into the office every day [are the ones who] show true leadership potential. In the situation we’re in now, it’s important that people consider others’ feelings and mental health in their decisions. And being able to ask for help is key: a lot of the time people want to come to a leader with the answers, not with problems. I would be impressed with someone’s maturity, emotional intelligence and vulnerability if they came to me asking for help.’

Louise Hewitt, Copy Director, McCann Health

‘This is the problem, what do you think about these options to fix it?’

There are two things that stand out for me when I am having one-to-ones with my team. One is when people proactively ask a lot of questions, full-stop. This tells me that someone is focused on making sure they properly understand the piece of work, and that they are keen to make sure they do that work well. Sometimes people are concerned that asking a lot of questions will make them seem slow on the uptake or overly anxious, but I would much rather answer lots of questions up front than have someone appear very confident but subsequently go off and do the wrong thing. The other thing that stands out are the people who identify a problem and then give me options they’ve thought about for how we might fix it. That’s a much better experience as a line manager than someone complaining and expecting to leave it with me to fix. If we work on it together, we usually get to a better, faster solution, and it also tells me that people will be great at leading their own teams in time. 

Deborah Wollard, Group Chief People Officer, MyRepublic
Deborah Woollard

Tell me more about your thought process. What are the broader context and considerations you are thinking through?

Asking such a question of a leader can be a great way to develop leadership experience and capability through learning first-hand from others. This is true particularly when they can provide powerful insights into their leadership approach and style directly through a real-life example. When you step back and allow a leader to explain the rationale for the decisions and actions they are taking, it enables you to build a greater appreciation for the context and take a wider view on things which you may not have direct access to. It also means you can learn from their insights and experiences — and the thought processes they have followed when they made certain choices. If the leader can share their thinking through stories and examples it is one of the best ways to absorb valuable leadership lessons and gain enormous learning in a 1-2-1. And it can also be a great springboard to ask great follow-up questions and relate back to your own experiences.


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