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WHAT YOU GAIN FROM ASKING: "WHY?"
Edition 029
FEATURED POST OF THE WEEK
Our long-form article of the week. You can always view the current and past featured posts on Empower’s blog.
The power of why: A strategic decision-making lesson from a toddler

Sometimes, your kids can provide valuable reminders about business best practices.
Recently, we’ve entered the era of “why” with our toddler—providing an unexpected reminder of how curiosity drives strategic problem-solving. A significant proportion of our statements or requests are met with the simple, one-word question: “Why?”
Then, we confidently answer, only to be met with…you guessed it: another “Why?”
This cycle continues a few times until our daughter either understands or we flip the question back on her—leaving her momentarily puzzled. The latter is always amusing, but it’s not the point of this post.
In Edition 005, I introduced the Five Whys framework and explained how it can be used to uncover the root cause of a business challenge.
My toddler’s current developmental stage has re-focused my attention on why this method of “probing” is important. It’s also made me think about the consequences of accepting situations at the surface level and the impact that has on progress and strategic direction.
For instance, take this one straightforward example from last year.
I worked with one of our partners to prioritize strategic, revenue-generating initiatives to help the business accomplish its 12-month goals. The team put forth a lot of fresh ideas, but we didn’t have the capacity, resources or time to do everything. We had to narrow our focus.
Can you relate?
In one team meeting, we focused specifically on this idea: bringing in an outside expert to conduct a workshop on a topic valuable to the membership community. We could charge extra and generate a new revenue stream during the months we hosted the workshop.
Here came my first “Why?”
Why do we think our members would pay to participate in this workshop?
After gathering perspective and historical context, we agreed there would be a willingness to pay.
Then my second “Why?”
Why can’t someone on our staff conduct the workshop?
The answer made sense. No one on the team had the certification or experience, which is key for this type of content and experience. As a result, we needed to hire an outside expert (i.e., higher cost and lower margin) to proceed.
This led to the third “Why?”
Why do we believe we can generate enough revenue to make this extra expense worth it?
This is where the conversation got interesting. As we examined the numbers and reviewed other workshops that generated higher revenue with better margins, it became clear—not just to me, but to the whole team—that maybe we shouldn’t pursue this initiative. It was shaping up to be more of a distraction than a meaningful driver of revenue and profitability.
There were probably five or more total probing questions during this entire discussion, but I won’t go into all of them. The point, however, is that had we not engaged in this dialogue, the team may have spent precious time, energy and resources on an initiative that wouldn’t have moved the business closer to its goals.
Instead, we made a more strategically aligned decision, narrowed our focus to core competencies and have seen success with members enthusiastic about the other offerings we launched over the past several months.
The lesson?
Be more like an inquisitive toddler. Apply curiosity-driven critical thinking in business by asking tough questions about key decisions, strategies and initiatives.
WEEKLY DOSE OF EMPOWERMENT
If you would like to submit a tip to be shared with the Empower community in a future newsletter, please reach out at [email protected] with the subject line “Weekly Dose of Empowerment Submission.”
Running it back to Edition 009: Make every meeting count
January is a good time for fresh starts and cleansing bad business hygiene. Making sure you’re using your time effectively, especially as it relates to meetings should be on that list. To help refresh tactics for how to make meetings more effective, I’m re-sharing our dose of empowerment from Edition 009.

Raise a virtual hand 🙋♀️ if you’ve never attended a poorly run meeting.
I obviously can’t see behind your screens, but I’ll wager no one reading this raised their hand. We’ve all been there at some point in our professional lives.
Here are three scenarios you’ve likely encountered:
You join a meeting and have no idea what it’s about.
You spend two hours in a meeting circling on topics but never land on a decision or next steps.
You try to ask the meeting organizer ahead of time for the meeting agenda and your role, but you never receive a reply.
A study by Reclaim.ai indicated the average annual cost of meetings per employee was nearly $30,000. Another article from Notta cited a statistic that stated only 30% of meetings are productive.
It doesn’t have to be this way.
While you can’t control everyone’s meeting habits, you can certainly control yours and you can strongly influence how meetings are run on your team and across your company.
The next time you organize a meeting, do these five things to make sure it’s a good use of time:
Define a clear objective and agenda in the meeting invite: In the description of the calendar invite, include a clear goal and specific agenda items you plan to cover. If you have an ask of the participants, it’s helpful to include those details as well. BONUS: If you want participants to show up thoroughly prepared to make key decisions, send prep materials 48 hours in advance for people to review.
Stay on track: Focus the conversation on the agenda topics. Create an environment where people feel comfortable contributing, but if the discussion veers off course, gently steer it back in the right direction.
Start and end on time: Set a professional tone and respect participants’ time by beginning and ending the meeting as scheduled.
Follow up and summarize action items: If you’re running the meeting, take the initiative to circulate a summary of the key discussion points, decisions and action items (with owners and deadlines assigned). Not only does this keep everyone informed and aligned, but it also reinforces accountability.
Be considerate: Ask people when they’re available for a meeting. If you have access to participants’ calendars and you notice someone with a conflict, do the right thing and reach out to see if their schedule is flexible. Don’t just double-book them. When you make assumptions, you’re communicating other people’s time isn’t valuable.
P.S. - If you lead a team or company, spread these best practices so everyone can benefit from better meetings.
P.P.S. - Be bold. The next time you receive a meeting invite and there’s no clear agenda, objective or decision to make, politely write back and say you won’t attend the meeting unless you have this information.
JESSICA’S READ, OR LISTEN, PICK OF THE WEEK
A little something that got my gears turning this week and might pique your interest as well!
From McKinsey: America’s small business — Time to think big
TL;DR
McKinsey put out this piece last October and it’s one I continue to reference in the new year.
The piece introduces the term MSMEs (micro-, small, and medium-sized enterprises), which collectively employ about 60% of the U.S. workforce.
One data point stood out:
MSMEs in the United States are only half as productive as large companies.
Only half as productive. Does it have to be this way?
There are fascinating differences in performance depending on region, industry and other factors. But, the real call to action is to make MSMEs more productive to boost U.S. competitiveness.
We could debate our opinions on how McKinsey presents a path to solving this productivity gap for this large segment. However, my takeaway is that smaller enterprises need trusted support and guidance. They need the tools to take practical action that will improve how their business runs so they can grow and compete effectively.
MSMEs already think big in many ways -- they want to take their business to the next level and they need the right resources to help them get there. At least, that’s what I’ve observed since I started spending a lot more time with emerging business owners.
JUST FOR FUN
Really, this section is just for fun. Who knows what will be in store each week?
Some of you may be located in more temperate climates, but brrrrr it’s been chilly here in Nashville recently.
To help fend off the winter blues, here are 10 indoor activities to try this winter:
Glass-blowing classes: I haven’t tried this yet, but multiple people have raved to me about how fun and interesting it’s been.
Go see a movie: Explore a theater with amenities and great reclining seats. It’s awards season after all, so there’s plenty to see on the big screen.
Cozy up with a good book at a coffee shop: There are few things I enjoy more than spending a couple of hours with a good book and a warm beverage this time of year.
Home spa experiences: There’s plenty of self-care to do in the comfort of your home that also doesn’t break the bank.
Host a game night: Bring people together and have a night of healthy competition.
Bake: Whether sourdough or a new indulgent baked good, try out a new recipe and treat yourself.
Hot yoga: You know what will warm you up and make you fit? A toasty hour in a yoga studio.
Practice your mixology: Whether cocktails or mocktails, there’s plenty of opportunity to experiment with beverage-making during winter months.
Plan your next trip: Give yourself something to look forward to and build the itinerary for your next adventure.
Visit a museum: Get a little culture and visit a new exhibit that piques your interest.
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