Name The Dilemma

One of the greatest blocks to interpersonal communication is our fear that we’ll hurt someone else or damage our relationships. This fear often holds us back from speaking up; giving feedback; identifying problems and asking for what we need. 

Since our startup life is an inherently human endeavor it will be full of interpersonal challenges that always involve or implicate at least one other person. As leaders, when we face an interpersonal communication challenge in particular, we typically take inventory of our options and identify two unpleasant choices: 

1 - Just Say The Thing. Take a deep breath, rip off the band-aid and take on an interpersonal risk that is worrisome or downright scary (e.g., hurting someone else or increasing the chance that person will disconnect in some way or even leave the relationship) 

or

2 -Don’t Say The Thing. Stay quiet and continue to tolerate or suffer the situation – whether it’s underperformance from a teammate or a situation where your needs or the team’s needs are not getting met.

When faced with these two unappealing options, many startup leaders spend a lot of time either in their own heads or with outside parties agonizing over how to decide between two unsatisfying options. Action is subsequently delayed or suspended indefinitely.

What most startup leaders don’t realize is there is a third option: Name The Dilemma. 

How do you know you’re facing a dilemma? A dilemma is any situation where you feel you must choose between unpleasant alternatives (usually just two, but sometimes more.) 

Interpersonal dilemmas are especially frustrating because startup leaders are consummate options-creators and problem-solvers. They are usually quite skilled at making tough decisions about code, product, strategy—but when human relationships are in play, those same leaders feel paralyzed or get stuck. 

The “Name the Dilemma” technique is this: 

Rather than choose on your own to “Just Say The Thing” or “Don’t Say The Thing”, you invite the other person into your dilemma and engage with them directly on how to resolve it together. 

I often see startup leaders struggle with interpersonal communication dilemmas they reflexively assume they need to resolve on their own. (e.g., “I want to tell this person X, but I am worried it will destabilize them or unnecessarily stress them out.” Or “I am torn about giving them this feedback because I don’t want to come across as <insert adjective describing bad person/leader>”) 

But here’s the thing: These dilemmas are impossible to resolve on your own because you can’t control how other people feel or think—you can only engage with them directly to find out how they are feeling and what they are thinking. And then, through dialogue, seek to influence each other. 

Sharing a dilemma and naming it upfront can engage others in a helpful and productive way. It enables the other person to tell you what they need, want or prefer—or they might even help you think of a more creative option for resolution that you would never have seen without them. The added bonus is that you’ll experience significant relief and not waste time by having to resolve the dilemma entirely on your own.

Stop trying to resolve interpersonal challenges on your own. Since those challenges are co-created they usually must be solved collaboratively. Use the “Name The Dilemma” technique as your opening and invite someone else to resolve the challenge with you. 

Not sure how to implement this technique? 

Check out the two scenarios below for some examples and inspiration:

Scenario #1: One of your employees is going through a tough personal challenge right now (could be a health issue or a family issue). That same employee is also underperforming in a way that’s negatively affecting both their work relationships and their work product. 

Just Say The Thing: In your next 1-1, you could plunge in, bring up the performance issues and start addressing them. You risk your employee taking it very poorly because they’re already stretched thin and don’t feel resilient enough to cope with the feedback. You risk them walking away from the conversation feeling angry, hurt or resentful towards you for appearing to prioritize company performance over their well-being.  

Don’t Say The Thing: You stay quiet. You watch metrics continue to drop week after week. You continue to hear from other teammates how frustrated they are with the underperforming employee. You feel mounting pressure to do something, but just keep punting and shielding the teammate from the truth of their underperformance and negative impacts on the team.

Name The Dilemma:  In your next 1-1, you “name the dilemma” with your employee and invite them to identify solutions with you. It could sound like this: “I am struggling a bit here because I want to be a supportive manager to you during this difficult time. One part of being a good manager is helping you navigate this period as best I can. Another part is making sure team performance stays high and team cohesiveness stays high even as teammates face challenges and distractions at home. I am starting to notice X in our metrics and hear rumblings of Y from other team members. So my dilemma is this: Do I postpone digging into this feedback with you given what you’re struggling with at home? Or do I dig in knowing that you’re stretched really thin right now? I haven’t been able to decide this on my own and I wanted to bring you into my thinking so we can decide this together. I care about you a lot and want to do right by you. Can we talk through together what’s the best way to navigate this situation?” 

[And then the employee might respond in any number of ways: 

• “I’m relieved you care enough to be honest and check in first and didn’t just launch in with all the feedback…”

• “I know I am falling short at work. But I want to do at least a little bit better even with the chaos at home. I actually could use your coaching/support on how to balance pressures at home and at work right now. Do you have any tactical ideas or suggestions for me? How could I triage better at work?” 

• “I am still unable to get my head above water and I don’t think I can handle this feedback right now. I also know it’s unfair to the team to put up with this forever. Can I have two more weeks to get my home life to a more manageable state? I’m taking action X, Y or Z to do that but just need a bit more time.  And then at that point let’s reconnect on how I can reset on that project and with those teammates.”]

Scenario #2 - You are under pressure to hire several engineers this quarter. One of your top candidates falls through at the final offer stage. Through back-channeling, you hear through a third party that the candidate declined the job in large part because they didn’t want to work with your co-founder who oversees the product team. You don’t have the specifics, but you start to worry about whether this will become a pattern and limit your ability to recruit. 

Just Say The Thing: You launch in and tell your co-founder everything you heard via the third party and express concern that something about how they are showing up in interviews is turning off engineers. You risk them feeling defensive or demoralized because the feedback is second-hand and vague, but still alarming and unclear how to take action to address. You risk them feeling resentful towards you for dumping this on them or distracting them when you know how much pressure they are under. 

Don’t Say The Thing: You choose to stay quiet. It’s only n=1 so far and you weren’t able to pinpoint specifics on the feedback. But it starts to haunt you a bit. You notice yourself extra cagey or nervous when your co-founder is about to head into interviews with potential hires. The stress of keeping this “secret” is also taking up some amount of cognitive load and creating stress for you. 

Name The Dilemma: You initiate a conversation with your co-founder. It could sound like this: “I’m facing a dilemma and I don’t know what the best next step is. I’ve received a single data point though a backchannel about why we lost an engineering hire. I’d like to talk about it with you in case there is an underlying pattern there, but the data point is pretty vague/low quality and might be hard for you to hear – so I also don’t want to cause you distraction or distress as there might not be a pattern here that’s worth paying attention to. How should we resolve this?”

[And then your co-founder might respond in any number of ways: 

• “Thanks for caring about me, but I definitely want to hear what you heard. Can you tell me?” 

• “I’m overloaded this week and can’t deal with this right now, why don’t we dive in if it becomes n=2 or if you get more info you think I need to hear? I trust you.”

• “Are you concerned that I am limiting our ability to recruit? If so, I definitely want to hear that from you and talk through your impressions. Let’s figure out together if there is something to address here or not.” ]

Note: In both scenarios, the “Name The Dilemma” option still carries some interpersonal risk as the “Just Say The Thing” option, but that risk is mitigated or moderated by the explicit clarity of your intentions and your desire to balance care for them with other responsibilities you have to the team/ company. Naming the Dilemma is not a guarantee that the other person won’t experience some form of negative emotion/reaction, but, if they do, it will usually be lower in intensity because they are hearing live how your intentions towards them are positive and caring. 

Photo Credit: BrianAJackson