Asking the right questions

Asking the right questions of yourself

By Courtney Ellett, founder and owner at Obsidian Public Relations

Welcome to a three-part series by Obsidian PR on “Asking the Right Questions: Getting the Answers You Need to Run a Successful Small Business.“

It sounds too easy, right? Ask the right questions and magic will happen? Yeah, we understand the cynicism about simplicity. But consider this – answers are knowledge. Knowledge is power. By having the right information from the very start, you’re in a position to make better decisions, lay a firm foundation and build something you’re proud of. Think of answers as real-time GPS for business strategy.

In future posts, we’ll address asking your team members and your clients the right questions. But for now, let’s start at the beginning. And if you’re far from the beginning of founding your business, don’t worry. Many of these questions will still be quite valuable. It’s never too late to adjust course and create a business mission and environment that is fulfilling on every level. Let’s begin.


You’re at the base of a mountain. Actually, let’s back up. You’re THINKING about climbing a mountain while lounging in your living room watching reality TV late at night. Your particular mountain in this metaphor is founding a business. Taking that leap of faith that’s been nagging at your gut for a while now. Long before you suit up and take the first steps on the ascent to the dream, the rigorous mental and physical preparation begins. There are no shortcuts. There are no fast tracks. Would you attempt to summit Mount Kilimanjaro without months and months (if not years) of prep? No, you wouldn’t think of it. (Side note – if you are interested in what it would be like to actually conquer the Seven Summits or attempt it, check out our amazing client Tom Lawrence on his blog about his climbing adventures.

Back to founding a business. You must start with asking yourself some very important questions before you step foot on your mountain. You’ll save yourself time and a lot of heartache if you don’t forget this valuable phase. Let’s be clear – this isn’t about doubting oneself or giving yourself excuses to NOT do something. It’s the opposite. It’s the means to the end. It’s the base camp to the summit. Let’s explore what that might look like.

Why am I even thinking about this endeavor? What does it mean to me? What does it represent? What will it achieve for me? There are so many entrepreneurs out there, and each has a different story about why they chose to start a new business. They were tired of their old job. They didn’t want a boss anymore. They were fired and had no other choice. They felt they had a unique skill set or solution to offer the market. They yearned for more financial growth and freedom. They wanted to better control their professional destiny. They wanted more time with family. They wanted a different lifestyle. They wanted to make a difference. Your story and your why might be included above, and many could apply. And there are so many others. What’s important is that you know your why and let it guide you because it could easily get lost among late nights and long hours, capital concerns, growth decisions, hiring and the organization’s culture. Always go back to your why.  

Do I have the skills and knowledge to go into this kind of business and be successful at it? Am I an expert or is this something that just seems fun? Even if I do know my trade, do I know how to build and run a business? Knowing how to bake is one thing. Baking for the masses is another. Making a product people clamor over and will pay a premium for is another. And running a bakery is something otherworldly. We’ve all been there. We taste the most delicious snickerdoodle (or coconut cupcake or doughnut or macaroon) or on the face of the planet. We enthusiastically encourage that purveyor of deliciousness by saying something along these lines: “Go open your own business. These will sell like hotcakes and you’ll make millions. Trust me!” But a scrumptious product doesn’t a good business model make. Yes, it’s absolutely a necessity to know your trade (baking, PR, wealth management, law, you name it), but so much more is needed for the recipe to work. Good business planning regarding scalability, costs, marketing, sales model, etc. has to be strategic and early. And it’s OK if you don’t know everything about running a business. Find trusted partners who can help. See below!  

I don’t know everything. Who can help me? How do I make this a success? How can I ensure I don’t make rookie mistakes? Finding trusted partners early on – before one cupcake is baked or before one building is designed – is imperative. Depending on your business focus, these partners could vary. But most will need bankers, accountants, attorneys, wealth advisors, PR/marketing firms, employee benefits firms, etc. If bricks and mortar locations are vital to the model, then so are real estate agents, architects, general contractors and engineers. Some entrepreneurs will need more intensive counsel with business coaches and specific industry advisors. Even if you’ve been in your sector for decades, these components are essential to creating the right trajectory. You don’t have the luxury – even despite zero cash flow – to avoid these partnerships. If you use money as an excuse, maybe rethink your capital position or your ability to go into business at all. These are not the shortcuts to take.

How do I grow? When do I bring on employees? Many small business owners make the mistake of delaying role delegation and team growth. They try to do it all and be it all for too long, which actually handicaps smart growth. At first, it’s widely expected for an owner to be a Jack- or Jill-of-all trades. I’ve been there too. But at some point, you must weigh how your expertise and time should be leveraged and when it’s time to hire others to do everything else. If you’re best at the operational side, who will grow your business? If you’re amazing at prospecting, who will lead the team? At some point, something’s gotta give.

Who do we want to be? What is our company culture and brand personality? This topic is a little trickier and is quite nuanced, to be honest. Many entrepreneurs have a laser focus on what they want to achieve as a business (revenue, market reach, etc.), but do most think about a purposeful shaping of a brand or company culture early on? Probably not; it’s icing or an afterthought. But it soon becomes at best a most defining characteristic or at worst a liability if not paid attention to and nurtured. These elements should permeate audience communication and internal operations. And for a small business, a brand and culture both start with the owner. And it’s not something to simply “establish” and move on. As soon as you think you have a handle on it, you try to grab the “cloud” of culture and brand only to find out they are more complex and elusive than you ever thought and can’t simply be engineered and herded upon demand.

Asking the right questions of your team

By Lauren Hannaford, Director of Client Services at Obsidian Public Relations

In the second piece of our series on “Asking the Right Questions: Getting the Answers You Need to Run a Successful Small Business,“ we’re taking a look at questions you need to be asking your team on a regular basis. Questions are the basis to any action. And you will have to take ongoing action to ensure your team is happy and productive. As you read, remember that employee happiness, engagement and wonderful company culture all look different for every small business — and that’s why questions are so important!

First, we know that every small business owner continually asks questions of their employees. What’s important here is that you are asking the right questions and identifying what you do with the answers. A great owner asks the right questions and then uses the answers to create positive change.,r at least respectfully addresses an employee’s answer that may not warrant change right now. An owner with room to improve may be asking questions but may not know how to best utilize the answers or doesn’t respond at all.

Second, conducting info-gathering strategies can be a challenge if this is all new to you! But, there are simple tools that can help small businesses achieve this with ease. Even small businesses with a handful of employees can roll out a number of different methods to gather employee feedback.

Finally, it’s also important to understand how your questions and your employees’ answers to those questions fit into the grand scheme of your business and your goals — and what that looks like on an employee happiness, engagement and productivity level. We are living and working in a time where culture, satisfaction and corporate responsibility matter. More and more, we’re seeing companies adopt new and innovative policies that address real-life challenges because ultimately it does affect the bottom line!

Here’s how it breaks down:

What types of questions do I need to be asking my employees?

The list could go on and on. You may need to create some categories — processes, culture, benefits/HR, technology, office space, business development and so on. From there, you can drill down to specifics. If you want to ask your employees about company culture, you may start by asking them how they feel about it overall. Beyond that, ask what specifically they like and don’t like — don’t avoid this step. Then ask what they value the most. Ask them what physical items or tools help them feel happy and productive at work. Which intangible incentives do they appreciate and which ones just don’t work for them and why? It’s also very important to ask if they do appreciate a certain “culture” benefit, how could it be better? Sometimes employees love celebrating each other’s birthdays, but the process behind it needs to change to benefit the whole team!

Don’t shy away from the tough questions either. Sometimes, the greatest outcomes are born out of asking one tough question. Like, what is your least favorite part of your role? Why don’t you think this team member is excelling?  

When you are thinking about the questions you need to be asking your employees, remember that every category or facet of your business works in tandem. Culture impacts productivity which impacts processes which impact achieving your goals.

How do I tackle this?

Once you’ve identified the right questions, map out a timeline to gather answers to each particular set of questions. You don’t want to overwhelm with a large annual survey. Employees could get fatigued and end up not providing strong feedback. Maybe quarterly works best for your organization, or monthly! That’s something you will have to test.

If communication strategies aren’t your forte, don’t worry. There are so many simple methods and tools to make this info-gathering stage easy. Here are just a few:

What do I do next?

It will be important to set a deadline to collect feedback and make it clear that employees are expected to respond to your questions in whatever method that may be. This process can take place in phases as well. For example, you can roll out a more general survey to your entire team to collect overall feedback on something. Then, you can set up one-on-one meetings to gather deeper details from each employee. Finally, once you’ve analyzed feedback and have an idea on the action you want to take, you can send a final email asking if anyone has additional considerations. After that, let them know what action you’ve decided to take and why! Closing that loop is vital.

It’s also very important to give employees the opportunity for open dialogue. You may conduct a short survey on a topic and then come together during a staff meeting to discuss so that everyone hears what everyone else has to say. This can be an efficient way to discuss and then make a quick decision on action necessary. At Obsidian, we have weekly staff meetings, quarterly leadership meetings and biannual retreats. We’re constantly asking questions of our employees through many different channels. We also have certain people who are part of the decision-making team, and that ensures after we’ve asked our team certain questions, we follow through and bring things to fruition.

The bottom line – asking your employees the right questions, carefully considering their answers and making decisions to enact change is a valuable process. It’s one that no company can go without doing and yet expect to succeed while maintaining employee happiness. After all, that’s what employees want to know – that you care about what they think and value their input. You show them you do by simply asking them questions.

Asking the right questions of your clients

By Taylor Jolley, Account Executive at Obsidian Public Relations

I’m convinced that in another life, I was a chef. I love to work with whole ingredients, laboring through culinary processes to make a final product that is magical. I’m building my personal recipe bank, learning new techniques along the way. Right now, I’m ever-so-gently dipping my wooden spoon into the world of sauces.

Sauces are intriguing, as the development of a sauce is equal parts science and art. Brown your garlic too quickly and your sauce will have an acrid taste. Cook your tomatoes on a high heat and you’ll completely change the flavor profile. And don’t even get me started on the order in which you add ingredients. It all matters!

And it was over a pot of marinara that I realized a fully developed sauce is a lot like a successful client relationship. It’s built over time, with care and a delicate process. You can’t dump all of the elements of a successful client relationship into a metaphorical pot, stir over medium heat and hope for the best. You have to work at it.

So, if a client relationship is a sauce, then the spices you add to your pot are the questions that we ask throughout the relationship. Without these questions, our client relationships will be bland, unappealing and borderline unsuccessful. But with careful thought and timing, peppering questions into your relationship will create a partnership that is, dare I say it, classic.

The art of asking questions is essential for professionals young and old to master. And I’m about to provide you a recipe:

Step one: Build a base for your relationship by asking fundamental questions.

I’m not going to say this lightly – the questions that you ask during your onboarding process are the most important questions you will ask throughout your relationship. These questions will create the foundation for all of your work moving forward.

You would think these questions would be naturally answered during the onboarding process. But I tell you from experience – a new client may not share this information unless you ask targeted questions. Without these questions, you won’t have a clear path to follow, and you’re prone to falling short of your client’s expectations.  

In our recipe, these questions are the onions and garlic you brown in olive oil before you add your whole peeled tomatoes. They are not the star of the show, but they are essential.

Step two: Throughout the relationship, taste-test your results and ask questions based on your findings.

Once you have a strong foundation, it’s our natural tendency to put our work into autopilot. But this complacency can be a slow death for any client relationship.

You need to continually ask questions about the work you’re doing to gauge success and ensure your client’s objectives still align with priorities you heard early on. Ask questions like:

As experts, we often assume our work is producing the expected results. And maybe it is! But if you don’t ask these questions, your work may be for naught.

These questions come at the point in our sauce-making journey where things are really starting to come together. It looks beautiful and smells divine. But you take a sip and, “WHOA,” that sauce needs salt! If you didn’t taste it, you may have never known.

Step three: Don’t be afraid of the heat! Sometimes relationships need fire-tested questions.

You just have to cook with fire at times! And in a client relationship, that means coming prepared with the really hard questions. Even if your work is producing results, if it’s not in alignment with a client’s expectations, they may be slowly souring to you and your work. Here are a few examples:

These introspective questions are hard to ask because the answer may contradict with how you view your work. Try to put your ego aside and listen to the answer. You’ll grow as a professional and strengthen your relationship.

In our recipe, this is the chile pepper we take the time to char on an open flame before we add it to the nearly finished sauce waiting in the blender. Working with the fire is scary, but the warm and smoky taste comes through in the final sauce – and it was worth a little heat.


So, whether you’re new to business or have been in the market for 20 years, I hope you’ve walked away with a desire to ask questions and listen more in all facets of your business. If you have questions about Obsidian or public relations in general, don’t hesitate to email us at insight@obsidianpr.com.

Bon appetit!