MSMP 86: Mark Herschberg on the Career Toolkit

Mads Singers Management Podcast

We often complain about the fact that there’s so much that “they” don’t teach us in school that we need not just for our careers, but for life. Turns out that instead of just adding one more voice to that chorus, someone decided to address those challenges by writing a book.

Today’s guest for the Mads Singers Management Podcast, Mark Herschberg, is the author of the new book The Career Toolkit: Essential Skills for Success that No One Taught You. Mark has managed to pull off a rare trick: 20 years in academia, teaching at MIT, and 20 years as a CTO, working with garage startups and Fortune 500 companies alike.

One of the aspects of our conversation that I found funny was how both Mark and I had to intentionally overcome parts of our own personalities in order to live the lives we do now. For me, as a classic introvert, I chose to ride a bus to work early in my career. I started with “Hi”s to strangers and when that became easier, I graduated to “Hi, how are you?” Mark’s technique was more dramatic: he used ballroom dancing. “If I made mistakes, it wasn’t the end of the world,” he noted. He took what may have been “high stakes” for others and turned it into a practice ground for himself. Not only did he become better at networking, but dancing gave confidence to his public speaking.

I shared that Toastmasters had been part of my own journey to improve in public speaking, and we noted that activities and hobbies like dancing or Toastmasters serve as their own form of networking. Rather than having to subject ourselves to the sometimes cringey world of “networking events” we have both come to realize over time that when you pursue interesting things you will run into interesting people. And before too long, you’re “networking” without even knowing it.

We also spoke about the value of negotiation and how some managers are “afraid” to train their employees to negotiate: “What if they use that against me?” But Mark really noted that this isn’t a smart way to think. It’s always better to negotiate against a good negotiator than a bad one. A good one figures out how to get the best outcomes for everyone instead of playing a zero-sum game. Yes, they may use their new negotiation skills “against” you, but they will appreciate your investment in them as a person, not just as a numbered employee.

Mark is so full of fascinating stories and helpful lessons that this episode could have easily gone on longer. I hope you enjoy it as much as I did.

Key Learning Points:

1. Mads notes that the best salesperson doesn’t necessarily make the best sales manager, and certainly can’t become one without training - 3:43

2. Mads shares that often when people say they “don’t like managing” it’s because they don’t know how - 5:20

3. Mark stresses the importance of being incrementally better than your competition rather than focusing on being the “world’s greatest” - 7:07

4. Mark used ballroom dancing to help with his fear of public speaking - 11:04

5. Mark gives us a tactic to get networking results without attending “networking events” - 15:05

6. Mark has been encouraging people to re-invest the time they have saved with Covid - 23:40

7. Mark talks about the importance of learning how to learn - 30:00

8. Mark goes back to memories of geometry in school to connect learning to life - 33:45

9. Mark makes the case for training your team to negotiate better (even if it’s against you) - 37:45

10. Mark points out that there’s no substitute for practicing what you learn in books, courses, and podcasts - 42:20

11. Mads talks about the prestige and advantages that come from hosting groups - 47:30

Resources Mentioned:

The Career Toolkit

3D Negotiation

Bargaining for Advantage

Start with No

Getting to Yes by Roger Fisher

Never Split the Difference

Good for You Great for Me

Connect with Mark Herschberg:

The Career Toolkit