Truthful career conversations.
12 powerful tips.


You may be the most approachable, well-intentioned leader with the greatest sense of responsibility for the well-being of your employees. And yet, there still remains the strong possibility that your employees simply don’t feel comfortable enough to be as honest with you as you’d hope. The truth of the matter is that managers aren’t able to know each of the different things causing stress for their employees both in and out of work. Nor of its impact on their employees’ decision-making process in relation to their jobs.

Say, for example, an employee has had several consolatory discussions with close friends who went into what they thought were protocol meetings, only to leave with redundancy notices due to the pandemic. The prospect of now having a formal discussion with their own manager may understandably cause some anxiety.

The best employees want to do well and progress. Consequently, when there’s uncertainty around the safety of their job, a career conversation may suddenly feel considerably more weighty. For employees that have been awaiting this conversation for a long time, if the manager is not able to offer career opportunities desirable enough for them, this can further impact the level of transparency given.

And if that’s the case with even your most dedicated employees, how much more for those who had been feeling unsure of their place in the organisation long before Covid-19? Or, those who have untapped potential that could be utilised, but are struggling with motivation and performance levels in a role unsuited to their skillset?

This is where career conversations become crucial to ensuring your workforce are on the right career trajectory that’s aligned to their own goals and vision. Which, is only possible in an environment that does not cause anxiety or fear around the topic. But rather, promotes one that’s supportive and is actively geared towards employee success and contentment in the workplace.

Here are 12 ways to achieve this.

1. Seize the moment and make it ‘human-to-human’.

Part of what can make these conversations seem so difficult for both parties is the solemn approach adopted within what can feel like severely formal settings. The best career conversations often happen outside of this, where the employee can feel under less scrutiny and pressure to give the answer they think their manager wants to hear.

These are some examples of semi-formal conversations to implement.

  • KPI meetings
  • Mentoring discussions
  • Check-ins following a performance review
  • Catch ups between meetings

2. Use buddies and colleagues so it is not always with their manager.

One way to sidestep the challenge of getting an employee to openly share with their boss is to simply allow them to have a conversation with someone else. This will spark ideas and help them rehearse their conversations and thinking. It can also challenge preconceived ideas or their outlook.

This is considered an effective means of drawing out an employee’s unencumbered perspective because they can feel confident they’re speaking with someone who is objective and without any agenda, other than to offer help. That allows employees to be more candid, and give truthful insight into where they’re at.

Somewhere down the line, a further conversation can be had between the employee and manager.

3. Don’t take it for granted that they know what they want and where they excel – you might need to help them.

Educating employees on their career options is a great means of building trust and transparency, which is key to holding quality career conversations.

By being upfront and helping individuals to look soberly at their careers with a full understanding of the pros and cons for each option they consider, you can help them get clarity around their goals. In doing so, you’ll help them plan how to develop themselves accordingly, and ultimately steer them towards the right decision for both them and the business.

4. Career development in the round.

Official career support is most vital at the monumental stages of their journey with a company. Such as when they’re just starting out in a new role, contemplating a change in direction and/or employer, or have recently completed some form of CPD.

Outside of that, lighter forms of support is more appropriate. This can take the form of projects, being in change teams; taking part in a development programme with a thinking partner, or being mentored.

Even you simply making the effort to ask them what they think can be hugely developmental and inspiring.

5. Focus on where they add real value and why you value having them in your team.

In the midst of the everyday challenges of life, it’s sometimes easy to slip into a static mindset and feel stuck. Use the conversation to bring the individual back to the core questions of who they are, what they want and their reasons for it. Doing this will help the employee move beyond their mental blocks, reduce their stress levels through addressing their underlying negative emotions and give way to more positive, action-orientated thought processes.

6. Ask how they can build on past experience.

Encourage the employee to reflect on their career so far. There are questions you can ask that will be helpful in achieving this.

  • Which skills are you confident in that you’d like to put to good use?
  • What would you want to do more of at work if you could?
  • What kind of work environment would you prefer to work in?
  • Who are the team members you most like to work with?
  • What values are important to you in the work context?
  • What did you used to do that you loved that you wish you could do again?
  • Which part of the company do you wish you could move to and why?
  • What do you most want to learn?

7. Give people a sense of direction and real purpose to their career path.

Reflecting on one’s career so far is just the first part of uncovering what will continue to drive them. Employees must also reflect on their overarching ambitions that stretch beyond their current day-to-day, much further into their future.

An effective career conversation offers a clear and tangible path that can merge the individual’s personal values and career aspirations. Thus, motivating them to develop themselves and work towards realising their larger goals.

8. It’s a two-way street, ensure you use the career chats to know what you need to do more of or less of, too.

Whilst it’s important for employees to develop self-awareness through meaningful reflection on themselves and their careers, managers must also have the capacity to do the same.

How well you’re able to do this will impact the level to which you can interact with your employee and hold a constructive, supportive conversation. That way, when you hold up a mirror for the individual, you’re much more likely to be met with an honest reflection of their strengths and weaknesses. It’ll also facilitate a more positive conversation that can help them to build confidence.

It’s worth noting that their learning is also your own learning. So, if you ask what they need from you too, inevitably you will grow and develop at the same time and they will feel partnered rather than managed.

9. Support building networks and knowledge of organisational structures.

The hybrid world of work means that it’s no longer possible for employees to feel like part of a team in the same way they would have done previously.

Supporting them in getting to grips with company dynamics, processes, and enabling them to build their own networks within the organisation is crucial to driving momentum across the business. Plus, it’ll assist in keeping everyone in the know about each other’s work and achievements.

Promote being connected, looking out to other businesses and enterprises so your team don’t spend all their time just looking in.

10. Make it bite-sized and evolve their career over four 90-day sprints.

You do not need to try and resolve everything in one long meeting – it’s often the case that important conversations take place incrementally over time. Think about initially beginning with a short discussion, as a pre-cursor to a lengthier meeting where you can delve into more detail with the employee and gradually progress towards a resolution. Plan quarterly catch-ups in line with their KPI’s. Review performance, development and career trajectory.

11. Make sure it ends with you both being clear.

So many

people walk away no clearer on their first step and action plan than when they walked in the door. What do you want to be the main takeaways from the meeting? Any successful conversation should lead to some form of action.

In the case of those centred on career development, the take-aways should be based on specific actions the employee can take that will progress their career development strategy towards their goals. As well as a mutual agreement on the measurables that will be used to assess their progress, along with a review date. Get them to write them down and send over to you, or to summarise them at the end of the meeting.

Don’t forget to do the same… What do you need to do to be a better leader for them?

12. Finally and perhaps most importantly.

Leave them on a high. Tell them what they bring, what you appreciate. How they add value and how you see their role in the future shape of the business. Inspire them, show them you want them – give them a reason to stay and build the role and the business with you.

Remember, if you are having a day when you are not in the best mood and are just in the wrong mental space for the conversation, postpone it till a day when you’re in a better place to positively impact their mindset and wellbeing.

Ask yourself: “What can I do today to help my employee Thrive and grow?”