#71 | How To Take Smart Risks With Todd Dewett

This week’s CWK guest, Todd Dewett, is a master of all things leadership. Many look to this author and reformed professor turned solopreneur for advice on being successful in and out of the workplace. He sat with the CWK community to share some of his most helpful tips and tricks on getting promoted, leading with empathy, and taking risks. His wisdom is sure to help you end the year strong and dominate in 2022. 

The Secret To Getting Promoted (7:25)

‘How do I get promoted?’ A question a lot of us are asking as we look over our goals for the new year. Contrary to popular belief we don’t have to be plotting or build up the courage to ask. According to Todd we should do this instead – 

“Ask your boss, ‘In what situation would promoting me be a no brainer? What new skills, accomplishments, project wins do I need to be focused on? What successes would bring me a promotion a few months down the line?’ Apply the advice they give and don’t be concerned with how long it takes, be concerned with being ready.” 

P.S. The same approach works well for entrepreneurs and business owners. 

P.S.S. Learn to share your new accomplishments on LinkedIn with my free Content Kickstart!

How To Check-in Remotely (15:12)

Staying top of mind in our new remote work world can be difficult. Todd says we can be memorable by switching up our approach.

“Variety is a hedge against faulty human memory. (Tweet this!) Mix up the way you interact and the topic of conversation. For example, call about something they’re working on, email to share something you’re working on, or meet to discuss an office event. Decide which channel is best for the other party and your topic of discussion.”

The Truth Behind Confidence (19:43)

Are you still a little nervous even though now you know how and when to approach your boss? Try Todd’s tips to boost confidence:

• Build skills + expertise
• Reflect on your wins
• Craft an environment of people that contribute to your competence and positivity 

Also, check out his Building Self-Confidence course on LinkedIn Learning.

Leading With Accountability and Empathy (28:40)

As an expert in leadership I had to get Todd’s take on holding people accountable while being positive and empathetic. 

“Standards are the first step because without them no amount of nice will ever create productivity. (Tweet this!) Have declared, clear, discussed, and mutually agreed upon goals to be reached by a set time. Then be consistent with upholding the standards starting with yourself, lead by example. Pay attention to your star players and your team members who missed the mark, but always start the conversation with how they did relative to the set goals. Do it lovingly, kindly, and respectfully.”

Evaluating and Preparing For Risk (37:05)

Stretching for something bigger and better always means taking a risk. Todd and I agreed it’s more valuable to take a risk and learn than to not and mull over what could have been. 

“Nobody interesting has avoided risk. They engaged them with open eyes, ready to learn because they know it will hurt a little before it starts to feel awesome. If it goes bad you’ll learn a ton about your competence and about how people who had to help you actually feel about you. 

If you prepare correctly, failing isn’t the end of the world. The people who regret risks are the people who didn’t prepare for it correctly.” (Tweet this!)

Todd shares more advice on evaluating and preparing for risk in his latest book, Live Hard.  

Speed Round (41:20)

• What have you started using or doing lately that you love? Waking up at 4 am
• What is the best gift you’ve given yourself in the last year? A wok
• What’s the next thing you’re hoping to learn? How to tell long-form stories
• What are your favorite social media accounts to follow? Stan Phelps, Sara Canaday, Marc Maron’s WTF podcast
• What are you hoping to accomplish in the new year? Learning delayed gratification and launching my new book, Kill the Monster

Homework: Think about what you need to stop, start, and change to be happier and more productive. Be sure to tag Todd & me if you decide to post your list on any social platforms.

Next week

As you prepare for the new year and the goals you want to accomplish, getting in front of your ideal audience is probably at the top of your list. Not to worry, marketing expert Brad Batesol will  be with us next week to discuss how to do just that and more. RSVP here!

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