6 Great Coaching Conversations to Guide Your Employees’ Careers

career counseling

Helping Employees Make Career Choices

As managers, our job is to get results, plan resources, and develop our employees.  In terms of effective employee development, the time we take to coach our staff members is critical to helping each one become a growing force within the organization.  Further, sometimes, we need to mentor them on more than just the day-to-day skills – we need to counsel employees on managing their careers.  When should they look for new opportunities?  How can we get our employees to own their own development?  Here are 6 great conversations you can have with your employees to help guide their careers.

RELATED: 25 Fantastic Ways To Develop Your Employees

1. ‘Focus on Experience, Not Speed or Title’

A talented former employee of mine was finishing an accelerated development program within the company.  At the end of the program, its participants had to apply for full-time roles within the firm.  In the case of this employee, it turned out that many of his peers from the program received positions at a higher job title than he.  The issue bothered him to the point where he considered taking a less interesting position to get a better title.  We sat down and I explained to him that title was not important – the experience and learning he would get this early on in his career would propel him far more than the title on his business card.

The Takeaway: One’s future positions and career growth are determined by experience, credentials and skills, not job titles.  When employees are new and in the beginning phases of their careers, it can be difficult to understand this.  Spend the time with employees to help them understand how a focus on skills and experience will serve as a catapult to his or her career.

2. ‘Once You Stop Learning, It’s Time To Move On’

Many new employees such as fresh college hires, are often uncomfortable with the idea of changing roles, or even looking for other opportunities.  They got that first job, but then what?  How long should they stay?  A key coaching lesson for your employees is the importance of learning as it pertains to career growth.  Careers should be fulfilling, and challenging, regardless of how many years you’ve been working.  Every new experience or skill is a new tool for one’s toolbox, and learning is a key component of keeping one’s career satisfying and engaging.

The Takeaway: During one on one’s with each member of your staff, inquire what he or she has learned recently, and what challenges they’ve been struggling to work through.  If you sense there are few challenges in front of them, ask what other opportunities they would be interested in to introduce new skills and experience.

MRH Recommended Book on Coaching:

Coaching for Performance by John Whitmore

John Whitmore’s Coaching for Performance
is a light read containing many great tips and concepts that will help managers improve their mentoring and coaching skills. John uses various sport analogies and other simple examples to help convey ideas concerning the role of a coach, the relationship between coach and coachee, and the importance of teams, all of which translate well into the business world. Of particular use to the reader are the numerous lists of bulletized questions and notes, which serve as a quick reference guide for the reader.



3. ‘Loyalty to Someone or Something is Not Reason Enough To Stay in a Bad Job’

We spend a lot of time at work, and with our colleagues.  Over time, we form relationships and bonds with many the people with whom we work.  But an employee’s career should be about himself or herself, not others.  Countless times have I heard someone say that while they don’t like what they’re doing, they cannot bear the thought of leaving their current team.  “I’d be interested in that opportunity, but it would put this team in a bad spot if I left.”  Or it may be “I’m not happy with what I’m doing but Mary’s been a great boss and I still would want to work for her even if the job isn’t the greatest.”

The Takeaway: While our employees may like the team they work with or enjoy working for you, if the job becomes stagnant and unenjoyable, it’s a sign they should move on.  Remind your employees that while noble (and appreciated!), loyalty should not override a great opportunity or a chance to do something different.

4. ‘How Do We Make You a 10 Year Employee in Just 5 Years?’

An old boss once asked me this question.  He was big on developing people and always tried to find ways to grow his staff’s capability.  He was a fantastic mentor and had a keen ability to help his employees identify their own weak spots, areas of strength, and hidden talents.  He would ask this question of his new employees to get the employee to own and chart his or her own growth plan.  The end goal, of course, was to find ways to accelerate each employee’s development.

The Takeaway: The faster an employee grows and gains experience – through diverse and challenging assignments – the faster he or she can take on more responsibility and contribute at a higher level.  Moreover, by having employees identify their own needs for development is far more effective than giving them a script to follow.

5. ‘How Do You Think You Add Value to This Team?’

We wrote an ARTICLE some time ago about how the most effective way to coach employees is through questioning – in other words, getting employees to reach the answers to open questions helps solidify plans more so than just directing or telling them.  Particularly with your younger employees who have limited experience, it’s sometimes difficult for them to have a clear sense of self-awareness.  Do they really understand how they’re doing, how they’re contributing to the team, or how they’re making the department better?  Asking an employee how he or she feels they are adding value will certainly prompt a response of uncertainty, but asking this will help your employees take a look into the mirror.

The Takeaway: As junior employees become more self-aware of their skills and how their unique talents and abilities help the broader team, it helps them make more deliberate decisions on how they can best contribute to and support future efforts.

6. ‘5 Years Ago, Did You Expect To Be Where You Are Today?’

Finally, here is a thought-provoking question to ask our employees when they struggle to decide if taking a new opportunity is a good thing.  Just as it can be for us, some employees may find fear in leaving a team or role they know and taking on a new assignment.  Sometimes, our job as career coaches, is to help give them a little nudge.  Everyone’s career path is different, and they often take unexpected turns.

The Takeaway: A great way to help employees overcome the fear of moving on – the unknown – is to ask them if they knew they would arrive at their exact position 5 years prior.  Most of the time, you’ll get a laugh and a response like ‘I would not have believed you if you told me I would be here 5 years ago.”  It’s an excellent way to give employees a little push in the right direction.

RELATED: 5 Things You Can Do TODAY to be a Better Boss

Great bosses are great mentors and coaches.  By helping our employees manage their own careers, we are developing our talent and building the overall ability of our organization.  Don’t just be a manager, be a career coach…


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