"Ask Diane"
Real Questions. Straight Answers.
On Sales
Why do so many small business owners struggle with sales?
Because they've been taught to think of sales as something you do to people — a process of convincing, persuading, or closing. That framing makes most business owners uncomfortable, and rightfully so. The real problem is the approach, not the person. When you shift to thinking of sales as a conversation focused on understanding what someone needs and whether you can genuinely help, everything changes. You stop dreading it and start doing it.
What's the most common sales mistake small business owners make?
Talking too much. Business owners are passionate about what they do, and that passion can turn into a monologue. The most effective salespeople spend more time asking questions and listening than they do explaining their offer. You can't solve a problem you don't fully understand — and the only way to understand it is to stop talking long enough to hear it.
How do I build a sales process that doesn't feel pushy?
Start by changing the goal. Instead of trying to close a sale, aim to have a real conversation. Your job in every sales interaction is to understand whether the person in front of you has a need you can genuinely meet — and to help them understand that too. A good sales process is really just a series of good conversations: an initial outreach, a discovery call, a follow-up, and a decision. When you take the pressure off yourself to "win," you become a much better salesperson.
How often should I be following up with prospects?
More often than feels comfortable, but in a way that adds value each time. Most sales are lost not because the prospect said no, but because the salesperson stopped following up too soon. A good rule: follow up until you get a clear answer — yes or no. Each touchpoint should offer something useful: a relevant article, a question you thought of, an update about your business. You're staying present, not pestering.
What's the difference between networking and prospecting?
Networking is relationship building — getting to know people, building trust over time, staying visible in your community. Prospecting is intentional outreach to people who fit your target market. Both matter. The mistake most people make is treating networking as prospecting — trying to sell at events where the goal is connection. Build the relationship first. The business follows.
On Leadership
What makes someone a good leader?
Self-awareness and the genuine desire to help others succeed. The leaders who struggle most are the ones who think leadership is about having the right answers. It's not. It's about asking the right questions, listening to your team, and creating conditions where people can do their best work. Good leaders know their own strengths and blind spots, and they build teams that complement them.
How do I hold people accountable without damaging the relationship?
Accountability isn't punishment — it's clarity. Most accountability problems start with unclear expectations. When someone knows exactly what's expected, by when, and what success looks like, holding them accountable is a natural conversation rather than a confrontation. When you have to address a missed expectation, focus on the behavior and the outcome, not the person. "We agreed this would be done by Friday, and it wasn't — let's talk about what happened" is very different from "You're always missing deadlines."
My team isn't communicating well. Where do I start? Start by listening — not to fix anything, but to understand what's actually happening. In most communication breakdowns, everyone is doing their best with the information they have. The problem is usually that people are operating from different assumptions, different priorities, or different definitions of success. Get your team together to surface those differences openly. Create shared agreements about how you'll communicate, how decisions get made, and what happens when something goes wrong. Then revisit those agreements regularly.
How do I manage someone who's resistant to feedback? First, look at how you're delivering feedback. Resistance is often a response to feeling judged or blindsided. Feedback lands better when it's specific, behavior-focused, and offered in the context of a relationship where the person feels respected. Second, be curious rather than directive. Ask what they're experiencing, what obstacles they're facing, what support they need. People who feel heard are much more open to change than people who feel criticized.
How do I know if I should hire someone or bring on a contractor?
The key questions are: How consistent is the workload? How integrated does this role need to be with your team and culture? And what's your cash flow situation? If the need is ongoing and integrated — daily tasks, client relationships, institutional knowledge — an employee usually makes more sense. If the need is project-based, specialized, or seasonal, a contractor is often the smarter move. Don't hire your way out of a process problem, and don't use contractors indefinitely when the work has become a permanent function of your business.
On Small Business
How do I know when my business is stuck versus just going through a slow period?
A slow period is temporary and often explainable — a slow season, an economic shift, a few big clients pausing. Being stuck looks different: the same challenges keep coming back, growth has plateaued over multiple cycles, or you keep working harder without getting different results. If you find yourself saying "I've tried everything" or feeling like you're running in place, that's a sign something structural needs to change — not just your effort level.
What's the first thing to do when business isn't growing the way I want?
Get honest about where your business actually comes from. Most small business owners think they know, but they haven't looked at the data carefully. Map out your last 10–15 clients: How did they find you? What made them say yes? What do they have in common? That exercise almost always reveals something — a referral source you haven't invested in, an audience segment that converts better than others, or a message that resonates more than the one you're leading with. Start there.
How do I get out of the day-to-day so I can actually work on my business?
You have to build systems and delegate deliberately. Start by documenting what only you can do versus what someone else could do with the right training and tools. Then, one at a time, start handing things off — to staff, to contractors, or to automation. It won't happen overnight, but every task you successfully delegate buys you time to think strategically. The goal isn't to remove yourself from your business; it's to stop being the bottleneck in it.
When should a small business owner hire a business advisor?
When you're too close to the problem to see it clearly. Most business owners wait too long — until things are really wrong — before bringing someone in. But an advisor is most valuable when things are okay and you want them to be better, when you're at a decision point and want an experienced sounding board, or when you're solving the same problem over and over and need someone to help you find the root cause. You don't need to be in crisis to benefit from outside perspective.
How do I define success for my business — and how do I know if I'm achieving it?
Success has to be defined by you, not by someone else's benchmarks. Before setting revenue goals or growth targets, get clear on what you actually want your life and business to look like. What does a good day feel like? What kind of work energizes you? How much do you need to earn to live the way you want? Your definition of success drives everything — your pricing, your client selection, your business model. Once you have that clarity, measuring progress becomes much more straightforward.
On Change & Growth
Why is change so hard for business owners to implement, even when they know what needs to change?
Because knowing what to do and being willing to do it are two different things. Change requires letting go of what's familiar, and familiar feels safe even when it's not working. There's also usually a fear underneath the resistance — fear of failure, fear of judgment, fear of losing what you've built. The most effective path through it isn't willpower; it's getting clear on what you actually want on the other side of the change, and making the cost of staying the same feel higher than the cost of moving forward.
How do I build a business that can run without me being involved in everything?
Systematize before you delegate. Document your processes clearly enough that someone else could follow them. Then hire or contract for the right roles, train thoroughly, and trust people to do the work. The hardest part for most business owners is the trust — letting go of the belief that no one else can do it as well as you. The truth is, some things will be done differently. That's okay. Done differently and done consistently is almost always better than done perfectly by you and not at all by anyone else.