January 13, 2023

Executive Spotlight: How To Deal With Difficult Stakeholders & Peers

In a perfect world, it would always be easy to deal with stakeholders, co-workers, bosses, and other peers. The truth is, sometimes we have to deal with difficult people in our personal and professional lives. How we deal with people, difficult or not, will be a factor in how far we go in our careers. So, how can we successfully deal with difficult stakeholders and peers without hurting our professional reputations?

We recently asked our leading executives how they deal with difficult stakeholders and peers at work.

Here are their responses...

Ana Smith, Talent Architect & Global Learning Strategist

Managing stakeholders is one of any project manager's most complex and important responsibilities. The success of any given project or initiative can frequently depend upon stakeholder collaboration and satisfaction, which is why it's essential to give careful attention to their needs.

However, managing difficult stakeholders and peers can be, and therefore become, quite challenging, so it's important to anticipate and manage them effectively. They might not be open and forthcoming in their communications, or they may only offer negative feedback. Some stakeholders may be frustrated at the progress of the project or may not seem to be very engaged in the work. These are some basic areas that you need to focus on in successful stakeholder management: identifying stakeholders (internal and external), understanding stakeholder needs, meeting their needs, underpromising and overdelivering, listening to stakeholder concerns, frequently communicating, amongst others. If not done properly, they can result in spectacular project failures.

There is an "Iron Triangle" on which experienced project managers focus on. This consists of 1) quality/scope, 2) budget, and 3) time. If stakeholders or sponsors want more in the deliverable (i.e., more features) then something has to give. The project will take longer, or it will cost more, or it will be a little of both. If they want to lower costs, they probably cannot do it without decreasing scope or increasing timelines. Stakeholders will need to understand that, and the project manager needs to be consistent on this point.

A poor appreciation of stakeholder management can often lead to catastrophic decision-making which ultimately leads to more cost, longer timelines, and diluted benefits.

Ana Smith helps people & organizations achieve their full talent potential by developing and co-creating people strategies and customized solutions, and turning them into impactful outcomes and collaborative relationships, using coaching as the "red thread."

Andrea Markowski, Marketing Executive

Coworkers argue about something during a work meeting

When I think of difficult people, my college job years ago as a part-time credit card bill collector comes up. People were often on their worst behavior when I called.

Thankfully, we were trained to handle these situations. In essence, you must listen to ALL objections before you can ask someone to agree to a request. It was a valuable lesson about human nature, listening, and empathy.

What does this look like, and how can you use this method?

Step one: Be patient and listen while someone might vent, complain, or express the issues preventing them from doing something.

Step two: Acknowledge what they’ve said and the feelings expressed.

Step three: Repeat steps one and two until there is no more air to clear. Do not move on until the upset person has had their complete say.

Step four: Transition to what you need and “what’s in it for me” (them)—a WIIFM—if they comply.

Also, never accept insults or rude language. In the bill-collecting world, we had permission to hang up if things got out of hand. In your real life, you have permission to leave the situation until cooler heads prevail.

Andrea Markowski is a marketing director with specializations in strategy development, digital tactics, design thinking, and creative direction. She has superpowers in presentations and public speaking.

Lynn Holland, VP Sales & Business Development

Man talks to a difficult coworker

Take a job, win a client, use a dating app, and you’re amongst people with hurts, hang-ups, and emotions like fear, anger, and insecurity near the surface. Add modern pressures and poof! Disagreement, bias, and attitude. An inevitable evil, here are some tools for influence and goodwill:


1. Seek to understand their POV and why (internal/external influences)

2. Suggest reaching the best company/collective outcome vs. personal preferences

3. Consider if ideas #1 and #2 can be combined for an even better solution (ideal outcome)

4. If #3 fails, translate #1 and #2 into their respective cost/benefit for the company/collective


1. Build individual profiles - job responsibilities, fears, and biases that internally motivate rejecting or buying into ideas or initiatives

2. Correlate ideas or initiatives to serving their inner personal interests without risk

3. Partner and collaborate with an internal champion motivated to build support for ideas or initiatives that improve the workplace

Lynn Holland is a business development executive with 18+ years of experience taking operational, IoT & retail technologies, products, & consumer engagement to market with a focus in petroleum & convenience retail.

Michael Willis, Sports Business Operations Executive

Difficult stakeholder gives the thumbs-down during a work meeting

How to deal with difficult stakeholders and peers:

1. The first step is to identify the stakeholder. While everyone on the team has value, I would identify the threat to the team. The overall mission and objectives of the team must be met. If there is a weak link, executives and team leaders need this information.

2. Like any other threat the team encounters, the difficult stakeholder’s activities must be monitored.

3. Meet them one-on-one to discuss the facts that have been gathered. Don’t just rely on second-hand information. Keep the conversation free-flowing. Let the difficult stakeholder do all the talking.

4. Determine the motivation behind the recent behavior.

5. Remind the difficult stakeholder of their place on the team and, most importantly, the mission and goals the group must meet.

6. Determine their motivation. Try to find out what triggered the behavior. Offer remedies or solutions.

7. Create a success story to create new energy and purpose. Tell the stakeholder how the team is valued and viewed by the company.

8. Develop a perpetual communication stream that flows in every direction. As executives, it’s our job to fix problems. But I feel it’s even more important to get ahead of issues before they become problems.

Michael Willis has 18+ years of experience working with accounting & sports organizations and has managed P&Ls of $10M - $125M+ with budgets of $3M-$50M+. He worked for the NFL for 22 1/2 years, mainly with the game officials working on the financial/accounting side of the business.

Mark Taylor, Product & Operations Executive

Coworkers talk about a project while a difficult stakeholder interrupts

“Dancing Monkey (DM): the length of time between giving someone work to do and your brain wondering why you haven’t seen any product yet.”

If a stakeholder’s DM works on a more frequent cycle than yours, they might come across as “difficult.”

To work out a stakeholder’s DM and stay one step ahead, use informal, face-to-face communication.

E.g.: “Accidentally” walk past their office the day after you were given the work.

YOU: “Hi, not stopping, know you’re busy...”

THEM: “How’s it going?”

YOU: "All good. By the way, I’m cracking on with that work from yesterday."

THEM: "Great. Could we review what you've done so far now/later/tomorrow/next week?"

(Here’s where you find out whether you’ll be burning the midnight oil—or if you have a few days’ grace.)

Do this a few times and you’ll soon become calibrated with a stakeholder’s DM, a means of managing their “difficult” tendencies better.

Mark Taylor has 20+ years of risk, technology, and product management experience working in global and regional financial services firms in the UK and the U.S. He's managed teams of 40+, successfully addressed 100+ regulatory issues, and has saved companies $15M+.

Lisa Perry, Global Marketing Executive

Coworkers argue during a work meeting

At this point in my career, I am an expert in dealing with difficult stakeholders and peers regarding how often this has happened to me in a work situation. That said, it’s never easy and takes patience, empathy, communication, collaboration, and your eye on the end goal to ensure you succeed. Here are a few tips I’ve learned that might help you with this situation:

  • Patience: The key here is to keep your cool as temperatures rise. Take the emotion out of the equation. If that means you need to step away, do it. It’s essential to be objective, calm, and professional.
  • Empathy: Remember the saying, “Seek first to understand, then to be understood,” from Steven Covey’s book, The 7 Habits of Highly Effective People? People want to be heard. Let them talk, and have them get their frustrations out. Even if you disagree, be quiet. It will be to your advantage. It’s important to understand where their negativity is coming from so you can address it. You will have time to speak. Give them the first round.
  • Communication Is Key: It’s essential to tailor your communication to their style when dealing with difficult stakeholders and peers. Ask them what works for them. I’ve also found that asking these two questions in emails helps clarify any miscommunication: does this match what you need, and did I miss anything?
  • Collaborate: Above all, you need to collaborate and show that you have their best interest at heart and you want to work with them and figure out the best path forward.

If you stay focused on the end goal and try not to get caught up in the emotional turmoil of dealing with difficult individuals, you might be surprised at how effective this approach can be.

Lisa Perry helps companies build leadership brands, driving loyal customers & delivering profitability. She does this through a process that builds brands consumers love. Her goal is to help companies develop, monetize, and grow their brands.

How do you deal with difficult stakeholders and peers? Join the conversation inside Work It Daily's Executive Program.

4 Ideal Questions To Ask In A Phone Interview

In every interview, it's important to ask questions. This especially includes phone interviews.

Asking questions during any type of job interview makes you seem more intelligent and interested in the job. It also makes you more appealing to hiring managers—as long as you don't ask questions you could easily find the answers to. If you ask the right questions, you also gain a strategic advantage. You can find out what the interviewer really cares about.

So, what questions are the best ones to ask?

Here are four ideal questions to ask during a phone interview:

1. If You Could Choose The Perfect Job Candidate, What Qualifications, Experience, Or Characteristics Would That Person Have?

You can simplify this question in a couple of different ways:

  • "What does your ideal candidate look like?"
  • "What's on your wish list for an absolutely perfect candidate?"

Some job seekers are a little afraid to ask this question because they don't want to highlight their imperfections—but that isn't what this question does. Their answer gives you a blueprint of what they really hope to find, which means that you can tailor all your answers to their questions much more closely than you could without this information. Your responses will stand out from the competition.

2. Why Did The Last Person In This Role Leave The Job?

Man writes down questions for a phone interview

If the previous person was promoted, what was their next job title? Is that typical? Is that where you'd like to end up? What did they do to get promoted? These are things that could help you know how to be successful in the role and decide if it fits with your chosen career path.

If the person was fired or left the company, the reason why may give you valuable information as well.

3. What Are The Biggest Challenges Of This Position?

Woman asks a question during a phone interview

Every position has a certain number of problems and challenges associated with it.

If you know what their biggest problems and challenges are, you can talk more effectively about how you can solve them and help the company. You'll sell yourself for the job.

4. From What You've Told Me, I Think I'd Be A Great Fit For The Job And I'm Very Interested. When Can We Schedule A Time To Discuss This Further?

Man smiles after asking a question during a phone interview

In any interview, it's important to ask for the next step. This question, or a version of this question, will allow you to show your excitement for the opportunity and eagerness to move forward.

By demonstrating your enthusiasm and interest, you'll automatically stand out to potential employers, and you'll actually give yourself a better chance of making it to the in-person interview.

Asking questions like these brings out information you can't learn anywhere else. They help you show your professionalism and interest in the job. Make a list of questions to ask and keep it in front of you during the interview. (That's one of the advantages of phone interviews—they can't see you.)

Along with these questions, you'll probably have a few more that specifically address that job. Just make sure to write them down so you don't freeze up and forget in the stress of the call.

Take the time to prepare for your phone interview and make sure you get invited to the in-person interview. Discover more phone interview tips and download a free phone interview prep podcast here.

Need more help acing your next phone interview?

We'd love it if you signed up for Work It Daily's Event Subscription! Get your career questions answered in our next live event!

Disclosure: This post is sponsored by a Work It Daily-approved expert and was published at an earlier date.

9 HR & Recruiting Predictions For 2023

At 1st, I believed it was the joke. I got a message from Chad Sowash and Joel Cheeseman , the co-hosts from the Chad & Parmesan cheese Podcast . This is actually the most popular podcast within the HR & prospecting industry. Reputed for being in a lather and filled with snark, typically the show offers a lot connected with insightful commentary on exactly what is happening in HR together with recruiting. In short, if you are in the field, it can smart to be hearing to the show.

So, whenever they invited me to sign up for them for their Jan 2023 Predictions Episode, My spouse and i was surprised. However, I just jumped at the opportunity to join in and observe if I could keep my own with 2 guys who aren't scared to say what these people think.

Just Call Me M. T. "Nostradamus" O'Donnell

I didn't choose the name, but When i did have a whole lot of fun trying to be able to predict what's going for you to happen in 2023. That i was asked to offer three predictions. I stored my BEST for final. HINT: It's all regarding LinkedIn and how As i think it's going to help give TikTok and Instagram creators a new method to make money!

Top 3 Chad & Cheese Podcasts Associated with 2023

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