Leadership Career Development Career Conversations

What skills do your managers need to hold effective career conversations?

In all our time working in the careers space, what we have come to learn about career conversations in the workplace is this: they're not happening nearly as much as they should.

One of the key reasons why this is the case is that leaders are not adequately equipped with the skills required to facilitate effective career conversations with their employees.

There are a number of requirements for career conversations to be successful. These are:

  • Trust: There must be a mutual trust between the two parties to facilitate an open and honest flow of communication and feedback
  • Challenge: Challenging the receiver on beliefs and behaviours is important and will pay off in the long run. Givers should avoid toeing the line and saying what they think the receiver wants to hear, particularly in giving constructive feedback about skills and potential. This is what many receivers need and value.
  • Relevant information: providing information about opportunities.


So what are the skills required to ensure effective career conversations are taking place in your organisation?

Personal qualities

  • Honesty, frankness & non-judgemental
  • Best interest at heart – does not toe the organisational party line
  • Affirming, positive stance

Understandably, employees look for and respond to different qualities in givers of feedback depending on their own personality, however there are a number of traits that were seen as instrumental in establishing trust and an open dialogue across the majority of positive career conversations in a study by Hirsch, Jackson and Kidd (2004). These are honesty, frankness and being non-judgemental. 

 It seems obvious to say that those giving career advice in career conversations must genuinely have the individual’s best interests at heart and no particular agenda of their own. This is where external givers can hold an advantage over internal ones, when there is no organisational agenda that needs to be upheld. For organisations that are political, sometimes it can help to engage the services of an external coach to give non-biased feedback.

CTA Career Conversations


In the study by Kidd et al (2004), the single most common complaint about unhelpful or negative career conversations was a lack of interest by the giver. This lead to the inability or unwillingness of the individual to form a valuable relationship with the employee and as a result prevented the giver from engaging on a level that was of any benefit to the employee. In particular, performance reviews were often seen as too haphazard and managers were criticised for not wanting to get involved in career issues. This further reinforced the belief that managers are not actually interested the careers of their employees. (Kidd et al, 2004).

Challenge and advice

  • Providing honest feedback
  • Thinking outside the box to push the receiver out of the comfort zone
  • Use of active interpretative skills
  • Encourage positive attitudes

Literature suggests overwhelmingly that employees want to be pushed outside of their comfort zone and value frank and honest feedback, even when it is tough to hear. Givers should not be too afraid of giving constructive feedback about skills and potential as this is what many receivers are looking for. After all, it is this information that will assist the individual to understand their own goals and career potential and align them with those of the organisation.

Employees in Kidd's study frequently referred to appreciating being ‘pushed out of the comfort zone’ and being helped to ‘think outside of the box’.  Pushing an employee out of their comfort zone can take a number of forms and may include challenging an individuals’ self-concept, perceived roadblocks to their advancement or their reasons for making particular career choices. 

Facilitative skills

  • Effective people skills
  • Listening attentively
  • Asking effective questions – show empathy

Facilitative skills involve listening attentively, showing empathy and the use of effective questioning techniques. These skills are all important in building trusting relationships and breaking down information sharing barriers. Some respondents described these as ‘people skills’ or ‘facilitation skills’, which left them with  ‘a warm feeling’ and gave them confidence that their concerns were being addressed (Kidd et al, 2004). Negative conversations were often characterised by a lack of listening and attention on the part of the giver. These facilitative skills were often viewed as being dependent on one another. For example, if the giver is not fully listening and attentive and asking effective questions, it would be almost impossible to really understand the employee's concerns. Another important skill within this subset is intuitive listening – hearing what is not being said just as much as what is being said.  

Information giving

  • Be specific with information
  • Allow for broadening of thinking
  • Examine how the information can relate to their story

The topics and advice given in many of the discussions reported in Kidd's study was very specialised, such as how to arrange an overseas exchange or how best to approach a certain HR issue. More often though, the career conversations were very broad and covered a range of relevant career issues. 

Employees reported that good givers of career advice broadened their thoughts about their careers and the businesses in which they worked. Career conversations with people who have a wide experience of opportunities both within and outside the organisation were seen as particularly valuable as they were able to share these different perspectives and open the employees mind to new perspectives and opportunites.  This was particularly true for external coaches or mentors, especially as they were not constrained by loyalties to the organisation.

Employees in Kidd's study noted that receiving information on relevant opportunities or contacts who could assist with opportunities within the givers network was also highly beneficial.

Honest feedback

  • Strengths, weaknesses and potential
  • Honest feedback with positive comments
  • Not to be seen as just “going through the motions”

An honest and analytical approach to giving feedback on strengths, weaknesses and potential is highly recommended, particularly coming from senior people. Providing honest and open feedback can work to inform employees of behaviours and traits that they may be unaware of or how their performance is perceived. Conversely, it is important that managers or givers of advice, are forthcoming with relevant and insightful feedback or they risk being perceived as 'going through the motions' and not investing the time and energy to assist the employee.

The effectiveness of the conversation is reliant upon the giver's ability to give open and honest feedback. This will be complemented by their interpersonal skills and their ability to soften critical feedback with positive comments about performance.  Others in Kidd's study were less worried about softening their feedback, but interestingly, some individuals still saw positive value in this..... At least with the gift of hindsight. For example, one manager reported that the feedback he received during an appraisal with his line manager, which listed all the things he was not good at, was ‘the worst experience of my life but also the best (Kidd et al, 2004). To further reinforce this theory, givers were criticised when they were not open and honest with specific feedback.

Management of the session

  • Preparation before the session
  • Set mutually beneficial agendas and prioritise issues
  • Create free-flowing conversation

The success of career conversations also depends upon the efficient management of the session. A process to manage the sessions needs to be established and agreed upon by both parties. This process might include preparation, communication or discussion about particular topics, and follow up arrangements.

It is important that discussions are designed to suit individual needs – a one size fits all approach defeats the very purpose of a career conversation. It may be advisable for employees to agree upon a suitable agenda to cover off the issues that are most pressing to them. Research suggests that employees appreciate the giver checking in that the individual is happy with the way the discussion is progressing. 

Feedback from many of the employees who had negative career conversations in Kidd's study was that the giver was more interested in their own agenda and overmanaged the discussion to suit their own needs, rather than letting the conversation flow freely.

Status, knowledge and experience

  • Share knowledge of organisation and HR
  • If relevant - establish a mentor that suits the career direction of individual
  • Share company strategy and experiences

In many positive discussions reported in Kidd's study, the giver's standing within the organisation was seen as beneficial to the discussion. Especially for senior givers, it could be assumed that this is because they have the power to open doors and advocate for the individual to others in positions of power. One individual, for example, saw her boss as a  ‘high-level guardian angel’ (Kidd et al, 2004).

Where possible, it is advisable for givers to draw on their often long-standing experience in the organisation. This could include recounting experiences from their own and others’ careers, explaining the company’s competency framework, and sharing knowledge about the organisation’s HR strategy (Kidd et al, 2004).


It is important for managers and leaders to reframe career development and make it a consistent feature in the workplace, not just quarterly or annually. When this is achieved and managers are equipped with the right skills to hold career conversations, this new way of conducting 'career development' is likely to produce positive outcomes in almost all circumstances. Positive outcomes may include increases in employee knowledge of his or her self, organisational opportunities, opportunities for development, and career management strategies for the future – all of which will significantly benefit your employees and organisation alike.

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