DESIGN SUCCESS FROM THE START: FIVE ESSENTIAL TIPS

Let’s talk today about setting people, teams and businesses up for success.

Entrepreneurial teams move fast and are typically lean. Especially in the earlier stages, there’s always more work to do than people or budget. At times, the pace is so accelerated that the focus becomes getting more bodies in seats to increase velocity, and key steps like clarifying roles, expectations or structured employee onboarding get overlooked.

The costly assumption? New hires will simply figure it out for themselves.

Putting off setting your people up for success rarely pays off. Instead, it hurts you, your team, the individual and the business.

Don’t believe me? This excerpt came straight from Gallup’s 2025 State of the Workplace report:

To flip to the positive, another Gallup article from last year indicated that the top-quartile of businesses, ranked for level of employee engagement, achieved 23% higher profits than those in the bottom quartile.

What drives employee engagement? Setting individuals up for success from the beginning.

Here are five tips for getting on the right side of this trend.

Tip #1: Provide clarity on roles, responsibilities and expectations

You aligned on a job description or scope of work when you made the hire. But that alone doesn’t secure high performance. Once on board, it’s time to double down on clarity.

• The role: Anchor on where someone fits into the organization and the value that role brings.

• Key responsibilities: Reduce ambiguity by concisely outlining what the individual owns and is accountable for delivering.

• Overall expectations: Be clear about availability, work product and communication norms. Your new hire isn’t a mind reader; provide the opportunity to adapt early.

• 90-day milestones: Provide focus and alignment in their first 90 days to effectively measure performance.

Without clear roles and expectations, you’ll end up answering the same questions on repeat and end up frustrated that your new hire isn’t meeting unspoken expectations.

Tip #2: Everyone needs onboarding

Whether a C-Suite executive or it’s someone’s first job, everyone deserves an onboarding experience when joining a company.

At a certain level, it’s tempting to assume experienced hires will onboard themselves. But no matter how seasoned someone is, they’re stepping into your systems, culture and workflows for the first time.

• Provide context: Ground someone new on how the business operates, team dynamics and other norms.

• Equip with tools and resources: Make sure all systems, logins and other resources are ready on Day 1.

• Develop a structured onboarding plan: This goes for the new hire and other internal stakeholders. Create a simple schedule a checklist for trainings, who to meet and tasks to complete.

Tip #3: Show them what good looks like

Your version of “good” might look very different from what your new hire is used to, and they won’t know unless you show them.

• Share examples: Provide templates, prior work and communication samples.

• Teach critical skills: Build role-specific training that sticks. Test for retention.

• Model values in action: Demonstrate how your mission, values and culture shape decisions. Make it more tangible.

If you don’t define good, you shouldn’t really expect to get it.

Tip #4: Centralize key institutional knowledge

In lean businesses, knowledge often lives in people’s heads or scattered sources. This slows down teams and fosters over-reliance on individual gatekeepers.

• Develop a single source of truth: This could be very simple (e.g., a Google Doc) or more complex (e.g., a Wiki built in Notion). Whatever the medium, what’s important is that new and existing team members have one place to look for key processes, ways of working, company info, FAQs, etc.

• Make it accessible: Share where to find information from Day 1.

• Develop a process for feedback and updates: Institutional knowledge isn’t static. It constantly evolves; refresh it regularly.

Tip #5: Provide early feedback loops

Feedback is critical, especially when time-to-impact needs to be short. Without it, missteps compound and become harder to unwind.

• Set weekly 1:1s or standups: These are great opportunities to surface challenges, sync on priorities and provide actionable suggestions.

• Find asynchronous opportunities to connect: Progress and feedback don’t always require a meeting.

• Make it a two-way dialogue: Shared perspective and understanding drives progress.

Intentionality upfront pays dividends

Take the steps now to avoid the frustration of rework, misalignment and turnover later. Your team will be more cohesive and you’ll give yourself an increased shot at success.

MEET MADELINE WESTFALL, OWNER, DESIGNER & PROJECT MANAGER OF MADELINE WESTFALL DESIGN

FINDING THAT ONE THING TO CUT

I’ve been thinking a lot recently about simplification. Understanding my most valuable resource is time, I’ve increasingly taken action to make sure it’s being used to its highest and best impact.

The question I’m asking myself regularly: What’s one thing I did this week that can, and should, be cut out?

Last month, the answer was:

• Cutting down on the time I spent on business development.

• Being honest about what had/hadn’t worked to date.

How did I adjust?

As many of you know, I’m a big fan of calendar chunking. I have a very colorful calendar, with different blocks that represent different activities. Purple = Business Development time.

Last month, I cut five hours per week of purple.

Does this mean I don’t do business development anymore? Absolutely not.

What does it mean? The remaining allocated time is now reserved for the activities with the highest ROI. I’ve cut out the “fat” to make time for other things that matter more for the business right now.

My challenge to you?

Ask yourself this week: What’s one thing I can let go?

Then, get rid of it and see what happens.

HOW 20 BUSINESS LEADERS PLAN TO FINISH 2025 STRONG FROM FORBES

TL;DR

Forbes interviewed 20 Forbes Business Council Members to understand their top goals for the year, all of which are outlined in this article.

There are great ideas here, but you know what struck me most? How many of them centered around business optimization (i.e., operations):

• Optimizing for profit.

• Leveraging automation and hiring to drive operational efficiency.

• Controlling the cost of supplies and expenditure cuts.

• Being a stable partner.

• Focusing and finishing.

• Reviewing the business plan and budget.

• Improving time allocation.

• Streamlining internal systems.

• Investing in the team.

• Deepening team alignment.

• Accelerating transformation.

• Integrating AI into business operations.

• Remaining focused on the bottom line.

Music to my ears. So often, entrepreneurs view operations as the ‘icky’ thing they don’t want to talk about. This article proves it’s being talked about in a real way as a strategic growth lever, and business owners want to take action.

ACCOUNTABILITY CHECK: 2025 RESOLUTIONS

At the beginning of the year, I committed to holding myself accountable to my New Year’s resolution by sharing progress updates quarterly in this newsletter.

As a refresh, I resolved to: Find at least one opportunity each quarter to volunteer my time. Whether through mentorship, getting involved in my community, or supporting a cause I believe in, I want this to be a year of giving back.

More than half the year in, and I’m still on track.

The Q2 update?

• I continued my work as the volunteer Partnerships Manager for Nashville Design Week.

• I became a mentor to an entrepreneur participating in the Nashville Arts + Business Council’s Periscope program.

• As part of OGC’s first mentor program, I served as a mentor for two women in that community.

All of these have been great opportunities to give back, and I’ve learned along the way as well.

How are your 2025 commitments to yourself progressing?

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If you’re ready to take the step, reach out to discuss how we can support your goals. 

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