#20 | Ask Me Anything With Kim Kaupe

I miss getting together in the conference room for birthday’s. You know, the cupcakes, the sparkling water, the small talk – that was my jam! However, more than the cupcakes (although cupcakes are delicious!) I miss the feeling of community and celebration.

I decided to recreate the conference room birthday party…virtually. Yes, I invited people to take a break and join me for small talk about life and fun. YOU were my amazing guest featuring cupcakes, candles and MORE. I’ve never done anything like this before so it was one of those figure-it-out-as-you-go moments! However, I’m happy to report my Coffee With Kim community pulled through (as I knew you would!).

Here were some Ask Me Anything Highlights from our chat:

If you could start over in your career what would you do differently? (12:50)

It’s hard to tell but I likely would have stayed in events. I love the checklists of the event world and seeing something from an idea, to a concept, to a production and then come to a close. You plan, execute and when it’s over there’s a sense of accomplishment I so enjoyed.

What were your favorite childhood books?  (17:47)

• Nancy Drew

• The Hardy Boy’s

• Boxcar Kids

• Eragon

• Harry Potter (still love this one!)

I loved these stories as I could lose myself in the world’s these authors were creating. When Richard jumped in with some more suggestions in the comments I was excited:

• Where the Crawdads Sing  (This one’s great I read it recently and couldn’t put it down!)

• The Passage

• Predictably Irrational

I’m a big reader and love new recommendations!

Who is the most unusual person you learn from? (21:47)

Bear Grylls. Yes you heard that right, the adventurer Bear Grylls. I wouldn’t necessarily label myself a “camper” by any means but I learn SO much from his wilderness adventures. He stays calm, cool and collected during situations that all of us (I like to think) would completely lose it over. He seems to embody an attitude of “I can handle anything life throws at me,” that I really admire.

I also love Mike Row from Dirty Jobs. He’s seems like a genuine person that you would want to grab a beer with. You don’t always get that feeling from the people you see on television but for me he seems to jump through the screen.

Jenn mentioned Ted Lasso, a fictional character from a new Apple TV show called, you guessed it, Ted Lasso, that would be good to check out. I’m always down to explore more entertaining homework! Thanks for this recommendation Jenn.

Most embarrassing moment in the corporate world? (25:25)

2 Situations Come To Mind:

1. Being Unprepared: I was caught off guard while interning for People Magazine and I’ve never forgotten it. I was asked a question about a current event that I was SUPPOSED to have read up on but of course didn’t. I was young and thought I could “coast” through meetings. As most people in business will tell you the one day you decide to “coast” is the one day you will get put on the spot in front of very important and influential people. It was so embarrassing and the lesson of coming to meetings prepared is forever seared in my mind.

2. Not Being Viewed As A Boss: A few years ago, after a great meeting with a potential client I kept getting asked one question over and over again. It completely confused me. The executive sitting across from me kept asking “How do we move forward with this?” no matter how many times I answered the question. Feeling frustrated and ultimately really confused, I finally stopped the meeting and awkwardly asked, “I’m sorry but what do you actually mean? I’ve told you how we can move forward about four times now.” Turns out, the man across from me was trying to “elevate the conversation” to my boss as a final sign off that we were good to go. He clearly did no research before the meeting and didn’t realize I was the owner of the company. There was no “boss” to get approval from! I turned bright red thinking “Man he really doesn’t see me as an equal or as a leader.” While I can now look back at it and laugh at my awkward inquires I realize now it was probably more embarrassing for him then me in the end!

What’s the best way to educate yourself on new areas before starting a business? (30:40)

If you can, rely on someone else. I call this the Avengers model. You never have one superhero that saves the day. It’s usually a combination of multiple heroes who swoop in to combine their forces to save the world. If you are Wonder Woman in this scenario find your Batman, find your Thor, find your Captain Marvel.

Find others who are experts in areas that you might need to learn more about. You can bring them on in a paid capacity, learn from them in a mentorship capacity or bring them into the business as equity holders or co-founders. If you can avoid learning and doing everything yourself.

How do I make an impact virtually? (34:40)

Here are 4 ways to nail your next virtual meeting:

1. Before the meeting, Google everyone on the invite. Time block at least 30 minutes to do this.

2. Research and locate each person’s LinkedIn profile.

3. Add a personal message about how excited you are for the meeting and Connect with them.

4. Try to do this BEFORE the meeting if not, make sure to do it after thanking them for their time and insights at the meeting.

In the pre-pandemic days, when having in-person meetings you were able to engage in small talk before and after meetings. Since turning to the person next to you and chatting a bit before the meeting starts isn’t possible we need to find a way to create that bond digitally.

Tip: Make sure YOUR LinkedIn is up to date! If you are asking others to connect chances are they will click on your profile and check you out. Make sure your information is up to date and details all the great things you’ve been up to at work. Set up a reoccurring calendar reminder to refresh your LinkedIn every quarter. I know it sounds time consuming but it’s worth it and will save you time in the long run. I have an awesome profile tip sheet here if you need help getting started on your profile makeover.

How do I ace an online presentation? (38:20)

This one can feel awkward and hard but here are my two best tips to bringing your best self to an online meeting or presentation:

1. Take time to get comfortable on camera! Practice. Get in a good headspace before you have to sign on. The jitters come through more online than they do in person and it’s much easier to “lose” your audience to distractions. Be as prepared as possible.

2. Your gestures and motions have to be a bit extra. Almost in an unnatural way as nuance is missed on video calls. Be a little bit bigger with your reactions. Start small and see how it feels.

What is New York City like right now? (41:20)

The long and the short of it, honestly, a bit weird. While outdoor dining is fun and the restaurants are doing what they can to make it great you can’t help but notice the streets are much more empty. I never realized how many tourists make up the foot traffic here until this month. Without the big cruise ships, tour groups and school trips hundreds of thousands of people are not in the streets or at the landmarks. You can see and feel their absence in the city. I’ve been updating everyone on my Instagram so if you’re curious feel free to follow along.

Next week:

Max Altschuler, Founder and CEO of Sales Hacker, has cultivated the world’s largest community of B2B sales professionals. With over 170k subscribers to his newsletter and not one, not two, but three books focused on the new age of selling under his belt he is a premiere leader in the next generation of sales professionals. If you’re curious about B2B sales or know someone who wants to up their game and learn from the best, you’re going to want to tune in!

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