Edit (21 Oct): Corrected a recommendation I made below to use Holland’s RIASEC in place of CliftonStrengths as they are not exact substitutes. The insights from VIA Strengths is more appropriate for such discussions

In my organisation, team leaders meet their charges once a quarter for a 1-1 conversation. Unlike a performance appraisal, the goal is not to tell you how you did. Instead, it is a coaching/staff development opportunity for bosses to help their staff work towards their career goals. Recently, I completed a 1-1 conversation and applied some career development theories which I want to share.

I used to think that such meetings were a waste of time. The most important thing to me was doing the job well. I thought the organisation would automatically appreciate my value and take care of my career progression. This was perhaps true in the past when everyone worked in 1 company for life. Today, rapid PESTLE changes have left many companies barely able to stay afloat, let alone invest in talent development. Bottomline: If you don’t own your career, don’t blame anyone if you aren’t progressing.

The 6 factors of PESTLE, courtesy of AnalystZone

This time, instead of letting the organisation decide my path, I tried a different approach. Having recently obtained my full CliftonStrengths® report, I decided to use the insights as a framework for discussion. If you don’t have a CliftonStrengths report, the VIA Strengths report is a good substitute.

My CliftonStrengths Top 5


1. Take stock of current reality.

Which strengths are you actively using in your currently role? I work on service innovation and technology, so a good part of my work is in IT project management. This allows me to flex my Executing strengths of Responsibility (taking ownership), Arranger (stakeholder and resource management) and to a lesser extent Restorative (improving service delivery). I enjoy this part of the work and would like to continue with it.

Are there areas of your work that you feel drained about using? A side requirement of project management nowadays is co-creating solutions to increase vested interest of the solution among stakeholders. This typically requires Communication and Includer, both of which are unfortunately not in my top 10. I prefer to take all the requirements and brew up a comprehensive plan on my own. Since I can’t avoid this, I flex compensating strengths like Harmony (seeking consensus) to manage. Otherwise, explore ways to outsource or avoid the work entirely if you’re creative.

2. Consider your goals.

What do you wish to achieve or how do you intend to grow? I’m not talking about vague goals like “I want to be promoted next year”. Instead, think about strengths you are not using, then consider responsibilities or training that would enable you to engage them actively. For me, this would be the Relationship-Building strength Relator (building close, trusting 1-1 relationships). In my organisation, some possible options to exercise it include a part-time career coach role or being a team leader. At this stage, keep your options open and brainstorm the possibilities, let your boss do the narrowing down later.

Over here, remember that you should think of and propose the options for your boss. As with other work issues, don’t present only the problem and wait for your boss to give the solution. More importantly it’s your career, don’t let somebody else take you for a ride.

3. Negotiate and put your plan to action.

Having done all the prep work, this is where rubber meets the road. Bring your proposal to your boss and discuss the options with him/her. Most bosses will be more than happy to give you additional responsibilities. Use the science of the tool to back-up your request, so you don’t appear lazy or overly ambitious. Most good bosses will try to meet you halfway as you explore options.

My boss and I agreed that l should not take the career coaching route due to capability and workload issues. Though I could not lead a team yet, she did assign me an intern. This provides a proving ground for me to flex Relator without worrying about permanent repercussions in case of mistakes. This is a win for me, a tangible step towards my career goals.

Parting thoughts

Maybe you’re reading this article and thinking: All well and good, but my company doesn’t have this practice… Stop there! Whether your company has this practice (and its true purpose) is irrelevant. The key is to involve your boss and borrow their resources and/or influence to help get to your goals. You don’t need a special session, a catch-up during regular meetings is good enough if you’re well prepared.

By using this framework, you show your boss that you take your career development seriously. Taking initiative and ownership to upskill and stretch yourself are important qualities of a good worker and leader. Who knows, this might give them the evidence and confidence to recommend the raise or promotion you desire.

6 thoughts on “Leveraging your boss to meet your career goals

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