Leadership Career Development Career Conversations

5 tips on how to have a career conversation with your employees that is effective and meaningful

Whilst it is widely accepted that employees must take charge of their own careers, career conversations are a two way street and organisations must get on board. Understanding the importance of getting these conversations right is vital for both employees and the organisations they work for.

CTA Career Conversations

How a career conversation is conducted can depend on whether there is a remedial focus, such as identifying and working through skills gaps, or a developmental focus, where the discussion focuses around lateral moves or transitions to align with the employee's career goals.

This is how to have a career conversation

Hirsh (2004) makes a number of suggestions for ways to conduct effective and meaningful career conversations without tacking them onto the end of an annual performance review. She advises managers and coaches begin by preparing well for the session. This will allow the manager to better hear the employee’s issues, before providing relevant information and opportunities specific to the individual. Providing honest and open feedback can inform individuals who are unaware of how their performance is perceived by other managers and colleagues.  She also suggests the provision of a management training program on how to handle effective career conversations with employees. We take a more in depth look at each of these below.

  1. Preparation before the session: Research suggests that preparation before the session, particularly by the manager, is an essential element that builds trust and rapport with the employee and demonstrates the seriousness with which they take their role. Preparation for a discussion could involve activities such as gathering relevant information, confirming a commitment to the process, establishing goals for the discussion and self-reflection about skills and aspirations (on the part of the employee). The manager may also find it helpful to speak with other managers the individual has been working with, reviewing utilisation reports and having a list of questions/conversation points to assist the employee to think strategically about their career. Some managers described how they felt it was important to ‘prime’ the individual before the conversation took place, so that they had time to think about the issues that would be raised (Hirsh, 2004).
  2. Quality of information: The information that employees look for in career conversations varies between individuals. Issues of work-life balance may be of concern to some whilst others may be more interested in understanding the wider aspects of the business or relevant career path options. It is important that managers are committed to having valuable and relevant discussions with their employees. Conversations where the employee perceives the giver is not fully invested and doesn’t care will likely impact negatively on the employee. In a study by Hirsh (2004), a number of managers went so far as to encourage people to think about their options outside the organisation. They were seeking results for the individual which were much wider than the next job move.
  3. Relevance: Of importance is a mutual understanding of how the employee’s expectations and aspirations fit with the business. When taking part in a career conversation, employees want information and career options that are most relevant and available to them at their particular career stage. Within the study by Hirsh (2004), skilled givers of feedback took into consideration an individuals’ strengths and career goals when providing information and advice. For example, one employee described how her manager ‘discussed with me the pros and cons of each position. She was able to give me her opinion on how each opportunity would affect my promotion prospects and she knew my personality and how I would fit in with each department' Hirsh (2004).  
  4. Career tools & techniques: In some instances, career tools or specific frameworks, may be used to assist individuals to think more about their career or consider their careers from a different angle.  It may be as simple as an organisational chart to help the individual visualise networks and career paths. Some managers and many external coaches use more sophisticated models and tools, such as skill and competency frameworks or visual representations of careers in the context of the individual's broader life. In the research by Kidd (2004), one manager used a particular technique to set the scene of the discussion which focused on long-term goals, asking ‘by retirement, what do you want to have achieved?’. The coach drew a line on a blank piece of paper and placed the employee's career issues above the line and broader ‘life’ issues below. The coach then focused the discussion around where the employee was on the line and where they wanted to be, both in work and in other parts of their life. A vertical set of lines was used by another manager to help individuals explore broader or narrower career options and lateral moves. Individuals also found metaphors of careers helpful. For example, one manager used the analogy of climbing a mountain to describe career development, asking questions about how far away the horizon was, the height of the mountain, and the tools needed in your back pack (Kidd, 2004).
  5. Clear plans and action: This point goes to the very heart of career conversations. Most employees want to see a clear plan for the future and take comfort in knowing that the career conversations are assisting them with this. It is important for managers to agree on clear actions with individuals before the meeting ends, giving the employee something to think about or work towards before the next meeting. Giving employees this time, sometimes over several meetings, to work through career issues demonstrated that both individuals and their career decisions were considered important. In Kidd's study,  ‘delivering’ on promised actions was reported by the employee as a clear signal of the giver's attitude towards the relationship. Where negative career conversation experiences were recorded, this was sometimes due to employees feeling their trust had been betrayed by a manager, who hadn't completed their agreed upon actions. 

When is it beneficial to use an external coach instead?

Up until recently, many held the belief that the most important discussions that employees would have would be with their manager in a formal performance review setting. However, we now know that this model is rarely effective, and in some cases, can actually cause more harm than good.  But what happens when effective career conversations can't be held for other reasons?


Where there is ongoing instability within the employee's organisation, the employee's reporting line is lacking people management skills, where the individual is dealing with deeper issues (career or personal) or for high potential (HiPos) employees, more targeted career support may be useful.

Career workshops, formal mentoring and external coaches may all be appropriate to support different individuals in different situations. When appointed thoughtfully, career coaches and mentors can have a significant impact on the employee through career conversations. Specialist support from career coaches can be particularly helpful for individuals to develop insights into their own skills and preferences.

Trevor-Roberts' career coaching programs empower individuals with the skills and tools to take charge and build an extraordinary career. Through career conversations with external coaches, individuals experience insightful, constructive and practical discussions about their career in a highly confidential and professional environment. The programs are supported by a suite of processes, assessments and materials based on decades of research and experience in the careers space.

Trevor-Roberts career coaches provide individuals with a range of tools and assistance through career conversations that result in:

  • Clarity about their future career direction & alignment with the organisation;
  • Enhanced self-awareness including strengths and areas for development and how these can be leveraged to achieve career success;
  • A reality check about the roadblocks and challenges to achieving career success;
  • Increased ability to deal with change;
  • Enhanced self-management in daily work and challenging situations; and
  • Pragmatic and specific actions on how to build careers.

A mixed approach to career conversations

According to Kidd's research, mixing up the way career conversations are held can provide overlapping positive benefits.  Conversations that occur with a variety of people in a variety of contexts and settings have a significant overlap in terms of the content they cover and the outcomes achieved. So what one person gets from a good boss, another might get from an informal mentor, an HR professional or an external coach (Kidd, 2004).


Within a typical organisational setting, it is imperative that managers make themselves available for discussions with employees about their careers. For effective discussions to occur, we recommend that managers foster open and trusted working environments with their employees. During these discussions, managers have a duty to plan and establish career plans that benefit the organisation as well as the individual, provide information relevant to the employee and ensure that appropriate skill development happens.

Overall, career conversations have been credited as being of significant value for both employees and the organisation. When they are implemented correctly, organisations give themselves a competitive advantage at a time of increased competition for high performing employees and in a cut throat, global market that constantly sees companies restructuring and adjusting to changing trend and markets.


CTA - Career Conversations - small



Discover the latest career advice, industry insights, and more

Leadership, Career Development, Career Conversations
Leadership, Career Development, Career Conversations
Leadership, Career Development, Career Conversations