With a new year should come a refresh on how program managers approach their work and how they engage with entrepreneurs. For seasoned program managers the following list might seem obvious but for anyone new to the field or in need of a reminder, keep on reading…
Program managers are nothing without the entrepreneurs who engage with and build through the programs they manage. Developing meaningful relationships and an atmosphere of trust with business owners is central to the success of your programs and health of your organizations. Entrepreneurs have limited time and bandwidth to work on their business while they’re working in their business. If your network does not trust that you have their best interest and outcomes centrally in mind, your time designing and managing programs may be unfulfilling and ultimately unfunded.
Cultivating an atmosphere of trust with business owners will yield an abundance of benefits for you, your programs, the owners themselves, and the strength of the broader community. You will experience increased engagement, improved outcomes, less friction, more robust data for reporting, warmer relationships, better referrals, and a killer network of business owners who have your back.
The needs, barriers, temperaments, and metrics for success vary greatly between business owners and across different industries and communities. How then, can you nurture trust with entrepreneurs as individuals and with the small business ecosystem as a whole?
Baked goods? The power of friendship?
Probably, but here are some common-sense practices that can help:
1. Make reliability a priority
As mentioned, entrepreneurs only have so much time to seek help while actively trying to build and run their business. Some local ecosystems have a wealth of programs, opportunities, and advisors to help while others have scarce resources where business owners may be wary of seeking outside assistance. In either scenario, you must be unwavering in your practice of following through on your obligations, whether it be the grander promises of a business development program or simply following through on an email response.
If you have a difficult time remembering all of the hanging email threads and programmatic promises you’ve made, create an accountability system for yourself with a project management CRM or even a nest of sticky notes on your desk, whatever works.
Because business owners have limited bandwidth, they likely will not continue to seek the support of someone who does not show reliability and commitment to their goals. If for some reason you’re not able to follow through on a promise or obligation, communicate and be transparent as to why. Make yourself known for your reliability and the trust will follow.
2. Design your programs with the entrepreneur firmly in mind
The content, goals, and setting for your small business program should all be designed with your entrepreneurial audience center of mind. You likely have specific funder metrics and accountabilities to leadership to hit but your funders and leadership look to you as the expert and your engagement and impact can only be maximized if your programs truly reflect the reality of your business owners. You may have data that points to a particular needed outcome or gap in the ecosystem but the most accurate way to design impactful programming is to seek direct input from those who you seek to serve.
Are you designing a program for growth-stage food businesses? Conduct a group listening session with five ideal food entrepreneur program candidates in your target area. Don’t know what workshops to schedule for the year? Make a poll and reach out to previous attendees and ask them what their goals and challenges are for the year and build around that. You are (likely) not some entrepreneurial oracle and you don’t truly know what your target audience needs until you ask.
Doing this alone will nurture relationships and help establish you as a trusted expert in the community before you run a single program. By skipping this step you risk creating programming that misses the mark, poor engagement, and eroding the trust of entrepreneurs who need your assistance.
3. Know your surroundings and make warm referrals (even if the entrepreneur has to go elsewhere)
Your organization has a portfolio of great resources, programs, and funding opportunities, but realistically you can’t help everyone with everything. One of the most important mechanisms for gaining trust from business owners is to recognize that you don’t always have what they need but you know where they can get it.
Having the grace and knowledge base to get that entrepreneur in touch with the most relevant resource demonstrates that you truly have their best interests in mind, regardless of where they receive the help. If you don’t have a great resource or referral in mind, saying “I don’t know but I’ll get back with you on this soon” is a powerful sentence (as long as you reliably follow up with them, see #1).
If you can connect business owners with the best possible solution, they will be much more likely to return to you for further expertise or better yet, engage with your programming when their needs align with your outcomes. An added bonus is that your partner organizations and colleagues in the ecosystem who receive the warm referral will be increasingly likely to send good candidates right back over to your organization.
4. Practice radical empathy
Entrepreneurs may generally have some common characteristics or face a similar set of challenges but do not make the mistake of thinking a one-size-fits-all approach will yield meaningful relationships. You may have studied entrepreneurship academically or you may have even been an entrepreneur yourself before running small business programs. That’s a great start but nothing can prepare you to relate to the unique circumstances of an individual business owner before actually taking the time to ask them questions about their business, their motivations, their history, and their ambitions. Don’t make assumptions and certainly don’t take anything personally.
Did you have a conversation where a business owner was skeptical, even defiant, about what they could gain from a program that you know would benefit them? Ask why! Maybe they still have a sour taste in their mouth from an unfulfilling experience last year.
Did an entrepreneur in one of your cohorts stop attending sessions with no notice or even a courtesy email? What happened? They could have been unhappy with the program, maybe they’re just flaky, but perhaps something happened in their personal life or they are struggling with balancing a full time job, family, their business, and your program.
You’ll never fully be able to walk a day in their shoes, but kindness, understanding through curiosity, and an empathetic mindset will not only build trust but will help pivot your perspective to better appreciating the entrepreneurial mindset on an individual and ecosystem level.
5. Be present in the ecosystem and celebrate milestones
Being a consistent cheerleader is a key component to relationship building and staying relevant in the small business ecosystem. It can also be the most fulfilling part of working with entrepreneurs. You’ve spent the time planning, designing, marketing, recruiting, managing, and graduating a small business cohort. You have earned the respect and recognition of the business owners who benefitted from your program. Should you just give them a firm handshake and wish them the best in their endeavors?
Follow them on social media, love their posts, hold the ribbon at their grand opening, visit their business when you can, recommend them to friends, patronize their pop up shops, check how they’re doing, ask what they need, offer what you can. You don’t just want to be a face anchored to an 8-week program. You want to be their champion. Their journey doesn’t end when your program does and neither should your support.
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Does this list seem obvious to you? Great! You’re doing the right things and building trust with business owners.
It is difficult, however, to remain consistent in these practices as the year goes on, as tasks pile up, as pressure from funders and leadership boils over, and as the program cycle fatigue sets in.
Make sure you’re being kind to yourself as a foundation and try to remind yourself that your work is important and you are helping others create new and better lives for themselves.


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