My favorite strategic planning questions

Dec 3, 2021

Here’s some of my favorite questions to ask when we are doing strategic planning work – whether it’s with clients or within my own biz.

Q1 – Why?

This one word is my favorite question of all time and I use it often. You have some amazing ideas of what you want to accomplish – why? It’s so easy to go from “let’s do this thing” to “alright, let’s lay out a plan”… but is it the right thing to do? Why is this important? Why now? If you (or your client) can’t answer the why question in a deep, meaningful way then I would hesitate to move onto in depth planning yet.

Q2 – How will we know if we are successful?

When we aren’t clear on what success looks like, we will never be successful. It’s not enough to have goals like “more money” or “more clients”. Or to “work less”.  Exactly how much money? How many clients? How many hours do you want to be working? Specifics are measurable and you can build your plan to work towards them. [This is also a great place to ask why as well – “I want to make $X next year… why is that important? what does more money allows you to create in your business & life?]

Q3 – What do I want my role to be in all of this?

If you are anything like me, you may default to doing way too much yourself. (yes… I am a recovering control freak. 😉 When you are planning it’s important to also plan for what you want your role to be. What do you want to do? Not want to do? What should come off your plate? (even though you could be doing it.) Give yourself permission to let go of the things you no longer enjoy and the places where you shouldn’t be involved anymore.

Q4 – Who can do this better than me?

This goes along with the previous question – as you clear your plate you will want to look for folks who can step in and bring their brilliance to the table. I like to look through the lens of “who can do this better than me?” vs. “who can I hire to do this” as it brings a different flavor/expectation to the table (and I promise you, there are always people out there who are better than we are at the things we should no longer be doing.)

Q5 – What if this doesn’t work out?

Yes, I’m all for big goals and having a positive attitude about it all. But I’m also a realist and like to spend some time considering the options if it doesn’t work out. What if we don’t reach our goals? What impact does that have on the business? On revenue? On me as a leader? What is our backup plan if we don’t reach our goals? [I’m a fan of having a list of ‘fastest path to cash’ strategies in my back pocket for these moments… as we all have them!]

I’m curious – what are your favorite strategic planning questions? Comment here and let me know.

Tina

PS: Heads up on a couple of things that you may be interested in…

1. I’m going to be having a ‘flash sale’ on 1-1 strategy sessions later this month – a 60-minute session for just $597 (I rarely offer standalone sessions and my coaching packages start at $3000 and up). If you are interested in getting some 1-1 time with me stay tuned…

2. I’ve got a monthly ‘mini retreat’ series planned for the new year, and am going to be offering a smoking hot deal if you sign up before the end of the year. These 3-hour virtual sessions are designed to be both affordable and highly impactful (I love when we can make meaningful change together in just 3 hours a month.)  More details to come…

3.  I have another round of the Certification Accelerator LIVE starting in the new year. If creating a certification is on your list for 2022 hit reply and I’ll put you on the early notification list.

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