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Pamela Ziemann
Energetic Speaking Coach for Entrepreneurs & NPOs
Bellevue, Washington
Very helpful
out of 10
14 votes

5 Tips for Having An Uncomfortable Conversation

The experts agree that having uncomfortable conversations is the best way to succeed in your business.
Written Oct 21, 2008, read 10621 times since then.


Did you hear Leif Hansen’s October 15th interview with Timothy Ferriss, author of The 4-Hour Work Week? Timothy talked about the importance of having uncomfortable conversations in this current economy and how it relates to small business success.

Personally, I think a lot of us come to life when someone mentions the unmentionable. Think of Seinfeld. They brought up so many taboo topics, they had viewers coming back for more. When I look back at my own business, I realize how it stagnated when I held back saying something that needed to be said. There’s something very gutsy and admirable about people who say what others might be thinking. Why don’t more of us do it? If you’re like most people, you've heard the old cliche, “If you don’t have anything nice to say, don’t say anything at all.” Well, those days are over. If you don’t want to be the 'nice guy' who finishes last, it’s time to learn how to have an uncomfortable conversation. You can do it without burning bridges and actually be more connected. It is possible to have uncomfortable conversation while adding a twist of compassion.

Here are 5 tips for making uncomfortable conversations a little easier for everyone.

1. Plan for it when you can think critically rather than emotionally. Set up a time that works for both of you. Tell them you have something important you’d like to talk with them about, what it is and about how long it will take. Having an appointment insures that you’ll be proactive rather than reactive. Just because you heard it’s a good idea to have an uncomfortable conversation doesn’t mean you’ll want have it when you’re stressed out. It can be tempting to send an e-mail, but it’s not the best way to have an uncomfortable conversation. After all, e-mail is a one way point of view (your view), conversation is two way. Letting the other person have a voice and then understanding it from their point of view helps them feel good about it too.

2. Focus on what will change because of having the conversation, not how uncomfortable it might be. Reward yourself for having the courage to initiate the conversation. You might even say to yourself, “As soon as I’ve had this conversation, I’m going to celebrate by… (The more difficult the conversation, the greater the reward!)

3. Put your attention on a common goal. If it’s a stressful situation and you’re really at odds with one another, you can always focus on how both of you would like less stress in your life. Keep in mind how this will help move you both forward. If you're reluctant to having the conversation, you might ask yourself, “What’s the payoff for me not having this conversation?” (e.g. pity from my friends, I get to stay small, etc. etc.)

4. Ask more questions with compassion. Not to be swayed, but to understand what’s going on for them. It’s easy to start assuming when we haven’t opened up the dialogue. The stories can get pretty elaborate in the circus of own minds. Maybe they’ve been looking for a way to bring it up with you. If you feel it’s uncomfortable, chances are they feel tension too. We don’t really know what’s going on for them until we hear it directly from them.

5. Plan enough time so neither of you feels rushed. Keep in mind the impression this conversation will have on your brand. While you’ve carved out enough time for this conversation, you'll also want to be deliberate on your next step. Leave when everything has been said and move on to your next goal. Don’t spend too much time replaying it in your mind.

Think of the last uncomfortable conversation you've had. What were some things that made it go well for you? What would you do differently next time? Thanks for sharing and adding to this conversation.

Learn more about the author, Pamela Ziemann.

Comment on this article

  • Brand Specialist • Creative Director • Founder 
Redmond, Washington 
Brandi L Pierce
    Posted by Brandi L Pierce, Redmond, Washington | Oct 22, 2008

    Great article, Pam. Always out doing yourself time and again. =)

    Most of my stories are a bit too personal to share, but I can honestly say that I can see how using these techniques would have made uncomfortable situations a lot easier to work through.

    I gave you a 10. I think this may have been the first 10 I have ever given to an article anywhere. Wow.

    I have a few articles that relate on a similar level, if you'd like to check them out at

  • Life, Prosperity, and Small Business Coach. Author. Speaker. Trainer. Singer/Songwriter. 
Seattle, Washington 
Kate Phillips
    Posted by Kate Phillips, Seattle, Washington | Oct 22, 2008

    Thanks for the article, Pamela, great tips.

    Can you say more about what type of conversations (besides "uncomfortable") Timonthy was referring to and how those conversations could move your business forward?

  • Creative Living Coach 
Toronto, Ontario Canada 
Jamie Ridler
    Posted by Jamie Ridler, Toronto, Ontario Canada | Oct 22, 2008

    There's real courage involved in having these difficult conversations. I love the idea of planning in a celebration as an acknowledgement of this brave step, regardless of the results.

    Hmm, it strikes me too that uncomfortable conversations aren't always about negative topics. Sometimes people can feel very uncomfortable sharing their love and positive feelings.

    Thanks for sharing some great tips on such an important topic!

  • Personal Coach, Life Exfoliator, Public Speaker 
Bothell, Washington 
Andrew Delany
    Posted by Andrew Delany, Bothell, Washington | Oct 22, 2008


    I am moved by your contribution, it's timeliness in my life, and how what you offers always relates to me in that flowy, intuitive way that I so enjoy!


  • Energetic Speaking Coach for Entrepreneurs & NPOs 
Bellevue, Washington 
Pamela Ziemann
    Posted by Pamela Ziemann, Bellevue, Washington | Oct 22, 2008

    Jamie, Bravo... I love your contribution of how uncomfortable it can be to share love and positive feelings. Let's have more of these conversations!

    Kate, It was a short 30 minute interview and they had a lot to cover. Timothy didn't go into a lot of detail, but when he said it, it was powerful. Maybe it's worth a second interview.

    Susan Scott wrote a book called "Fierce Conversations - Achieving Success at Work & in Life One Conversation at a Time" There's a lot of good references in her book.

    Thank you for sharing all your thoughts.

  • Information Strategist 
Higley, Arizona 
Charlene Kingston
    Posted by Charlene Kingston, Higley, Arizona | Oct 23, 2008

    I completely relate to your statement about holding back from having an uncomfortable conversation and watching my business stagnate. I had a challenging client who put me in situation after situation where I had to be the one who initiated a series of uncomfortable conversations. I can say that I learned a great deal, and it transformed my client relationship. Not to mention how it boosted my confidence in my ability to run my own business. I love your list, and I think anyone open to learning to do this will be greatly helped.

  • Certified Residential Specialist 
Bellevue, Washington 
Jan Radosevich BA, CRS
    Posted by Jan Radosevich BA, CRS, Bellevue, Washington | Oct 23, 2008

    Pam, Very timely post about being courageous. Good job Jan ;o)

  • Self Promotion Expert 
Hoboken, New Jersey 
Ilise Benun
    Posted by Ilise Benun, Hoboken, New Jersey | Oct 24, 2008

    Pamela, excellent tips that would help anyone tackle an uncomfortable conversation.

  • portrait and fine art photographer 
Bellingham, Washington 
Jeanne McGee
    Posted by Jeanne McGee, Bellingham, Washington | Oct 24, 2008

    Great tips Pam. I know that when I have had to have one of these "uncomfortable conversations" that the worry I put myself through with the "thoughts" of having to have the coversation are worse then what the conversation was really like! In fact, it always feels so good after I am done that I laugh with myself over the sleepless nights I gave myself.

    And you're sure right, about preparing yourself ahead of time (what questions to ask, how to say what you need to say in a non-threatening way etc) it is so valuable and makes the conversation go a lot easier.

    Thanks for the article.

  • Blogging Coach and Copywriter 
Seattle, Washington 
Judy Dunn
    Posted by Judy Dunn, Seattle, Washington | Oct 24, 2008

    This is helpful advice, Pamela. You are right. Being honest (and courageous) enough to say what others are thinking is a good thing. A person who does this is respected in the end.

    I admired my best friend and teaching colleague because she always just brought things out in the open (but in a good way). If something was bothering her, you knew it. Surprisingly, that just made people trust her more because she always showed her true self.

    I'll remember your 5-step process next time I need to have a "conversation."

  • Photographer/architectual/residental/commerical, Graphic Designer/Pshop/QuarkX/InDesign, Pastel Artist 
Renton, Washington 
Thomas Willa
    Posted by Thomas Willa, Renton, Washington | Oct 25, 2008

    Pamela, Difficult conversations are great to have when a positive attitude is at one's base. I appreciate the steps to guide one through these conversations Although, for me the passion and pride of my photographic creations sometimes are difficult to temper. I recently was accused of being conceited about my product. I had to state that after years of committment to pursuit of excellence that I have real confidence in creating images for products, events and of people. Sometimes these difficult conversations just pop up. I think I will be a little better prepared for when they do after reading your article. I think steps 2,3, and 4 would be great to recall in those moments. Thanks.

  • Artist 
Redmond, Washington 
Mike Schwagler
    Posted by Mike Schwagler, Redmond, Washington | Oct 25, 2008

    Hey Pamela- I'll score you a perfect ten on this wonderful article! I've been in various businesses over the years and (although I never really analyzed it in quite this way) having difficult conversations always leads to closer relationships, referrals and more business.
    Actually, conversations that appear to be difficult (to the observer) are often quite easy when you have the benefit other person in mind rather than yourself.

    On the other hand, I totally agree with Jamie, when it comes to expressing love and positive feelings we hold back...and then sometime later, be it moments or years, we regret we didn't share the sentiment. Why is that?

    Perhaps the difficulty isn't in the conversation, but rather in the fear of the conversation. We have to face up to a potential rejection or to the end to a relationship. That's tough stuff for the ego.

    Christine Comaford-Lynch in a recent teleseminar (I'll have to revisit the recording to get her exact words) said to tell eveyone you love that you love them. Now wouldn't that make this a perfect world? -Mike-

  • Effectiveness/ Business  & Awareness coach 
Norwalk, California 
Bruce Leonard
    Posted by Bruce Leonard, Norwalk, California | Oct 25, 2008

    Pamela, I love the idea of uncomfortable conversations. This is how we grow. I know for myself I look for the uncomfortable in the comfortable. Thats where the juice is. Being honest with communication with others is a win/win situation, the message gets delivered and I get to stand proud and tall for being true to myself. Acknowledgement is a huge key to momentum the next time opportunity comes a knockin.

  • Freelance writer 
Oakland, California 
Stephanie Stiavetti
    Posted by Stephanie Stiavetti, Oakland, California | Oct 27, 2008

    Great article! Often difficult conversations have the most amazing potential for growth. Thanks for this.

  • Personal Space Organizer 
Seattle, Washington 
Allison Faye Nelson
    Posted by Allison Faye Nelson, Seattle, Washington | Oct 29, 2008

    Thank you for bringing up such a great topic. There IS so much potential for growth, both personally and in opening another level of honesty in one's relationship to another human being.

    I feel compelled to share the biggest thing I've learned about approaching uncomfortable conversations, which relates directly to what Jeanne said:

    For all the time you can spend worrying about what you (and someone else) are going to say, to really express the difficult thing takes usually less than 30 seconds. With practice, it becomes like jumping in a cold river. It's normal to feel the excitement and hesitation before taking the plunge, but it's always worth it.

  • Structural Engineer 
Bellingham, Washington 
Charles Waugh
    Posted by Charles Waugh, Bellingham, Washington | Nov 18, 2010


    This was a great article -- too bad it took me so long to see it (as I was looking at some of the all-time biggest attractions on Biznik).

    Write more!