6 Expert Insights

(1) Play to their respective strengths, utilizing those as the rationale for any decision you have to make.

(2) If possible, toss the situation into their laps and allow them to develop a solution to present to you.

(3) Ask each of them what they would do if they had to make this decision.

(4) Promote both, with clear-cut roles & responsibilities; before the promos take effect, have them meet to discuss their expectations of each other and develop a code-of-conduct that they'll both adhere to in their new roles as "Co-"

A few keep concepts will help you here:  Empowerment, Engagement, and Understanding.
- Determine with them the need and partner with them on solutions.  
- Ask them how they suggest working in the new format
- Seek input on concerns and overcoming them
- Put ownership over pieces of the process in their hands.

When two people are candidates for one promotion, it's hard to avoid a perception of winning and losing. That must be the objective of your difficult conversation with the candidate not promoted: framing the situation as an opportunity, rather than a loss. Since your DRs have complementary skills, it should not be a stretch at all to emphasize how much the company values both contributions. It would be very helpful to have a career path to discuss so your valued DR can see a compelling future with your company.

No matter how well you manage your difficult conversation, it may well happen that you lose your DR who is not promoted. Egos and emotions are in play, so you need to consider that scenario. Then have an honest, respectful heart-to-heart conversation and don't forget to listen!

Situations like this often cause us to lose a bit of sleep, but what helps most is having a plan. One place to start is to have a clear Job-Description, this will allow you to measure each individual against what you are really wanting in that position.

There are also some tools that will allow you to measure each individual against what you are really looking for which can assist you in the decision process. What is important is to use as many tools as possible in making your decision. Too often we only use our gut and our heart, we much also use our heads.

Prepare for the very real possibility that the one not promoted will leave, notwithstanding your best efforts to avoid that outcome.

If s/he does leave, you'll be that much more ready to minimize (and better handle) the disruption.

If s/he stays, you'll be that much more convinced you were right in choosing who you did to promote!

In either case, it's a case of the needs of the business trumping the wants of its employees. And there's no shame in articulating that bit of clarity to the affected parties.