Your Field Guide to Difficult People: 10 Questions to Win Them Over & Get Ahead

 Build your reputation, grow your influence, learn and get ahead by building solid relationships with the "difficult" people and leaders who few others take the time to get to know. 

Build your reputation, grow your influence, learn and get ahead by building solid relationships with the "difficult" people and leaders who few others take the time to get to know. 

You’re reading this because you care. You care because you want to make a good impression, do good work, build your reputation on authenticity and (let’s be honest) you want to get ahead - but…

There’s a pain-in-the-butt influencer or stakeholder who keeps road blocking you. 

Getting in good with difficult people can be your career’s single biggest strategic advantage. Just imagine, you have them on your side, the unattainable advocate in your very own Survivor-style alliance.

If you make inroads with the difficult influencers who no one else has access to, then you gain exclusive insight to their perspective, insider knowledge, and access to otherwise unattainable resources - and - they’ll stop roadblocking you and instead work to support your objective. 

These questions can be the key to open doors with the PIA’s in your life. They’ll drive your conversations forward and elevate your relationship.

Use with caution. These questions have the power to change the trajectory of your relationships, your reputation, your career and your life.

 Growth (e.g. in your career) means expanding beyond your comfort zone. Learning to build relationships and communicate with the "difficult" people can be one of your career's single biggest strategic advantage. 

Growth (e.g. in your career) means expanding beyond your comfort zone. Learning to build relationships and communicate with the "difficult" people can be one of your career's single biggest strategic advantage. 

QUESTION #1: How are you doing?

WHY: There's something magical in adding the "doing" in this question. It makes it more personal. It's a little more sincere. Where "How are you?" is so often a conversational obligation "How are you doing?" is really asking about their day, their feelings, their overall status. Even if you don't get deep, you learn tidbits to use to build a shared bond (“yeah, my inbox has been crazy too” or, “I know, Verizon sucks”) and call back to when you talk next.

QUESTION #2: What's keeping you up at night?

WHY: Hello. Here we go. This gives you a beeline to their pulse points. This is what you can help them solve and therein is your key to win them over and forever be someone who "gets" them.  

 The difficult people you work with have strategic insights, resources and advice that few others - if any - have access to. Build those bridges and you'll have your very own Survivor-like alliance. 

The difficult people you work with have strategic insights, resources and advice that few others - if any - have access to. Build those bridges and you'll have your very own Survivor-like alliance. 

QUESTION #3: What's your IDEAL solution? 

WHY: It may be lofty but you have to know the best case scenario so you can a) understand why it’s preferable vs. all the others and then, b) work to accomplish it (or some feasible variation). The magic here is that you create shared dreams, shared vision, shared motivation for attainment. Welcome to bond-building. 
BONUS TIP: Throw in a little shared understanding. Validate and live in the dream with them, “Oh, yeah! That’d be great because [insert insightful strategic advantage here, to demonstrate you understand the value].

QUESTION #4: If we don't [act], what will that [be/look/sound/feel] like?  

WHY: Where are the land mines? What's the boulder chasing their Indy? Similar to shared motivation for attaining the best possible, you’ll build trust and allegiance to share their motivation for avoidance.  
BONUS TIP: You can add this to your stick arsenal for carrot-stick motivation later "You want to avoid … so we need to [action]…" when you want to persuade them not to do something.

QUESTION #5: How is this situation different?

WHY: Why is this particular kerfuffle different from all of the others they experienced before? Different players, drivers, timing, resources, marketplace? You gotta to know what you’re working with but even more important – you gotta know what they think they’re working with. 

QUESTION #6: What about this surprised you?

WHY: Maybe nothing and maybe everything. This is your sneaky-nice strategic way to dig into how much this person contributed to the problem. #1 - Are they surprised? What did they miss? Why? Are they out of a loop or running rogue? This is what you have to get ahead of, prevent going forward and, or rectify. Or, #2 - No surprises and they're ahead of the game.

QUESTION #7: Tell me more.

WHY: Not really a question. It's a request. And to get in real good, use this at least once per conversation. This is magic. There's always more. Even if you think you've heard it all. Even if they start repeating themselves. Communicating is hard and to clearly convey a thought and supporting reasoning is even harder. The more you hear from them, the clearer you'll be on their real intent, the full story, the moving pieces, the risks and rewards. It's giving them a practice-run plus a bonus double-check.

QUESTION #8: So what I'm hearing is…, is that right?

WHY: Like "Tell me more" but the reverse. You may think this question is stupid or redundant. You're wrong. Humans want to be understood. So - prove you understand. And be gracious when they give corrections because edits help everyone in the long run. When they modify your summary, it’s their opportunity to improve and not a reflection on your listening skills. Read: You give them an extra opportunity to be heard and you demonstrate that they’ve been understood. Classic win-win.

QUESTION #9: How likely are you to…? 

WHY: Once you understand the options at-hand or pitched a proposal, you want to know what you're up against even before you get to the gate. So ask. 
BONUS TIP: If you're feeling fancy, throw in the old 0-10 scale. You can follow up and ask why they chose that #. If the #’s encouragingly high, you may not need to follow up. If it's low (like 7 or less) dig in a little - gently. “What could we do to make that a 9?” Or "What support would you need to make that more like an 8?"
This gives you a peek into Pandora’s box without the risk of opening. You learn their resistance points and then are able to address them directly. You also hear why they think it’s a great idea and spin that to reinforce their motivation to act. 

QUESTION #10: What advice do you have? 

WHY: This is elegant. And classy. And humble. You don't have to take their advice but it always makes people feel good to be asked. It's an honor, actually. You demonstrate that you value their perspective, their experiences and (whether or not you care what their advice is) you present yourself as an ally. 

Which question's your favorite to break down walls and get-in good? Have you tried any of them or do you have your own special list? Would love to hear from you. Pop on down to the comments and share. 

If you are interested in more ways to lead, engage and motivate, check out the preview chapter of my new book (releasing early 2017), “How to Be a Bitch Whisperer: Your Guide to Winning Over Difficult People” by clicking here. 

Our specialties are helping you manage the difficult clients and other people in your life, client and team engagement and motivation, client relationship expansion (deepening existing revenue streams), referral growth strategy, retention strategy, attrition and crisis mitigation. 

For specialized solutions for you, your team or your clients, please reach out at tarah@tarahkeech.com