Comfort with ambiguity: Setting Expectations to get what you want

Josh Macintyre is a 2015 Fellow Alumni & Head of Revenue Operations at Grammarly, which provides digital writing assistance tools, sits down with Scott to discuss how Canadian Tire helped him direct his career impact and provided career clarity. Going back and forth between business school and work, Josh was able to gain a clearer understanding of the type of management role he wanted to step into. From building relationships to managers setting clear expectations for their employees, finding the right mentor to help with your career or professional growth, and providing value to others, Josh gives us an insight into his career progression and the significance of enjoying what you do.

Season 1 — April 26, 2021

Three Tips on Finding Career Clarity

Scott: What are your best tips on gaining career clarity?

Quickly try to understand which aspect of the roles you take on suited you. Try different things while in school, but look out for what doesn’t work well with your skill sets. Strengthen what you’re good at and be hyper-aware of areas that need improvement.
Finding out what you like and don’t like is essential to build your career based on your strengths. How? Keep a running list of daily things that challenge you and things that don’t motivate you and positive and constructive feedback.
Look out for what Josh calls “clickable skills.” If you’re slightly interested in the leadership route, take in different roles to learn to identify solutions from various viewpoints. Then, learn how to apply these transferable skills to your next position.

Three Tips on Managing a Team

Scott: What recommendations do you have for managers on leading and motivating teams to be as high-performing as possible?

Set clear expectations. Be clear about the end goal and set an expectation around the outcome and process to get there. People can’t read minds, so communicate as clearly as possible. How? Try setting up Objectives and Key Results (OKRs).
Give your team autonomy. Ensure each team member knows where their work needs to get to in terms of the quality of the work and your expected outcomes. Help them understand how they can get there.
Take a situational management or leadership approach to manage your team. Ask each team member how they prefer to work. Your role is to ensure they perform at their best instead of being too rigid on how you think they need to work.

Three Tips on Stepping Into Mentorship

Scott: You’ve referenced Todd Finch, Managing Partner at The Main Thing, and how he’s played an important role in your career as a mentor. What advice do you have for seeking out, finding, and developing mentorship-style relationships?

Understand which area of your life or career you need mentorship. Once you know what you wish to mentorship on, demonstrate a genuine interest in having someone as a mentor. Then identify they are interested in mentoring you. How? Make an intentional mentorship request.
Commitment comes hand in hand with mentorship. It’s not going to work if there is interest but no capacity. The relationship should naturally evolve if it’s working, don’t force something that doesn’t fit.
Foster an honest relationship with your mentor and allow feedback to happen on both ends. Mentorship is a two-way street. Ask how you can also add value back to your mentor. What are ways you can help them?

Here are Josh's favorite picks:

A Promised Land: A riveting, deeply personal account of history in the making by Barack Obama Shoe Dog: A deep dive into Nike's journey from an intrepid start-up to one of the world's most iconic brands by Phil Knight Barbarian Days: An account of an obsession, a complex enchantment by William Finnegan

Highlights

"Attending school in a smaller place helped me grasp the essence of relationships" 6:15

"Setting clear expectations and listening to individual needs can assist managers and leaders to better motivate their teams" 10:20

"Mentorship is a two-way street - both the mentor and mentee should have mutual interest" 18:25

"Try enjoying being in a organization with a lack of structure; not just be comfortable with it" 22:45

"Slow down. Listen More. Be more thoughtful about the future." 38:08

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