

By Arden Reynolds
April 8, 2025
Ask & Assert:
Tools for being a trusted advisor at any stage in your career
When you’re still learning the world of marketing and communications, it’s easy to feel like you're either executing someone else’s vision or trying to prove you belong in the room. But what if there was a model that helped professionals—regardless of title or tenure—show up with clarity, build trust, and contribute meaningfully? In this conversation, Joshua Reynolds shares the core of what it means to become a trusted advisor and introduces the Ask & Assert model: a practical, honest framework that helps you know when to get curious with questions, when to lead with assertions, and how to earn trust through both. What follows is a candid, experience-backed discussion about how less-experienced professionals can act as a trusted advisor without compromising authenticity.
Thank you for taking the time for this interview. I want to start with a basic question about trusted advisors. What does it mean to be one, and why is it important?
Joshua Reynolds: Being a trusted advisor means you're giving your client what they actually need in addition to what they asked for. And there's often quite a difference between those two. Executives sometimes think they understand marketing or PR, but they’re missing a crucial slice of the picture. As professionals in this industry, it's up to us to know what they actually need.
So, being that trusted advisor means you don't just do what you're asked. You help them figure out what they should be doing and guide them to that understanding.
It's important for a couple of reasons. First, the right thing won't happen if people without the right expertise are calling the shots. Mistakes get made, and people don’t get what they need. Second, it makes doing your job the right way much more difficult, because you’re working towards the wrong end and will likely have to go back and correct it after all is done. And third, it’s just more fun. You’re leading the client—not out of ego, but because it's how things get done right. It ensures a better chance of success, deepens the relationship, and furthers your career.
You don’t just meet expectations—you set them. You don’t just solve problems—you help define them. Basically, trusted advisors know when it’s time to step up and lead.
Interesting. It seems a proactive role, but one with more than a couple potential pitfalls. What are the challenges to becoming a trusted advisor, and what makes it harder to be trusted?
Joshua: One big challenge is that, at least in marketing and communications, the work you do is often misunderstood and undervalued. People think that because they can talk or write, the job will be easy. As a discipline, it doesn't get the respect it deserves. We're in the business of persuasive storytelling. There's both an art and a science to that, and without experience and awareness, it can lead to two common mistakes.
The first is being overly deferential. When you ask an executive, "What's the message here?" you're making them the marketer. You are handing away your expertise. Instead, you want to ask, "What are we trying to get done here? What's the business outcome?" Suddenly, the vision still comes from them without capitulating your expertise in how to best get that vision communicated.
The second mistake is on the other side of the spectrum: being overly assertive. This can look like a couple things—stepping out of your lane, asserting on things you don’t fully understand. Just because you’re in marketing doesn’t mean you set product strategy. Respect the boundaries and respect your own limitations.
It really comes down to finding the balance. At Rob Roy, we use the Ask & Assert model in our training that distinguishes between client service and client leadership, balancing the mindset of both of these pitfalls to strike a stronger, balanced approach.
So, the Ask & Assert model. What is that, and where did the model come from?
Joshua: The core principle is simple: when you're closer to the truth of something, assert it. When someone else is closer to the truth, ask them. Ask & Assert is the inhale and exhale of earning trust. You ask. You assert. You go back and forth. Sometimes you lead with assertion. Other times it’s curiosity first. The key is knowing which to do, and when.
For example, ask your client what their business objective is. They know that best, that’s their expertise in this situation. But then you might assert a communications strategy to help get it done. Ask who the target audience is, then assert what you know about that audience. Ask what the client wants the audience to think, feel, and do—then assert your message strategy.
I learned these lessons the hard way. I was in leadership training back at Hill & Knowlton and came in way too confident. I thought I had all the answers, didn’t ask a single question. From business objectives to what they’d want, I overasserted. Five minutes into the first mock client meeting, the "client" leaned in and said, "Do you even know how to ask a question?"
All the blood left my face. I was humbled—and quickly. But that moment taught me the importance of curiosity and listening. Since then, I’ve used the model and the principles behind it every day.
Sounds like a rough lesson! With that type of faceplant in a meeting, it does raise the question: are there risks of using the Ask & Assert model incorrectly? Of it “misfiring”? Essentially, can you use the model wrong?
Joshua: It rarely misfires—if it’s used with the right intent. But if you’re using it to look good, people will spot it immediately. I’ve seen it. In one of our Rob Roy trainings, someone asked questions just to draw attention to themselves. It didn’t work and wasn’t a good look.
There’s a concept called the trust equation. Trust equals credibility + reliability + intimacy, all divided by self-orientation. If you're using this model to serve yourself, that denominator increases—and your trustworthiness shrinks. The person in that training was increasing the self-orientation dramatically. Regardless of how reliable and credible their concerns were, it was hard to see the questions they asked as an authentic attempt at learning more.
This trust equation seems inextricably linked with this concept of authenticity. What role does authenticity play in both Ask & Assert and being a trusted advisor?
Joshua: Authenticity is the backbone by which the Ask & Assert model builds trust. Beyond the model, it’s how you build trust in general. All the model helps facilitate is you being honest and not pretending to know everything. You care enough to ask thoughtful questions—and you're brave enough to speak up when it counts. That’s authenticity, and that’s what earns trust.
And being a trusted advisor? That comes as a byproduct. You don’t wait for someone to hand you a "Trusted Advisor" plaque. You start acting like one today. You start with being authentic and curious.
Can someone be a situational trusted advisor, or do you always need to be in that role?
Joshua: Excellent question. You always want to be trusted, but you don't always have to be an advisor. Sometimes, if a client asks for a social media post to promote an event, you don’t need to stop everything and evaluate it. You just do it. Maybe you ask a few smart questions to do it better, but you're there to get it done.
But if they’re asking for the wrong thing—like a press release for a product that doesn’t exist yet—then you need to step up. You’ve got to help avoid a bad outcome. The key is keeping your "trusted advisor sensor" on at all times. Ask yourself: Is this the right thing to do? If yes, go ahead. If not, you speak up.
What if someone doesn't feel like they have anything worth asserting or they’re not the expert in the room?
Joshua: You never assert just for the sake of asserting. You assert when you have something genuine and useful to say. And if you don’t, you don’t fake it.
But often, even if you’re early in your career, you’ll have something to contribute. It could be as simple as saying, "I don’t understand," or "This doesn’t feel right to me."
You don't need to assert something profound in every meeting. Sometimes you're just there to listen and absorb. But this is exactly where the Ask & Assert model comes in handy. You’re always going to be closest to some truth, even if it’s not what is immediately discussed right at that very moment.
From one interpretation, it seems these models could ask people to sacrifice aspects of who they are. Is this the case?
Joshua: It goes back to authenticity. I truly believe everyone has a truth to assert, and anyone can ask a powerful question. The model works for every kind of personality. Apply parts of the model to you, not parts of yourself to fill the model.
If you’re more introverted, you may lean toward listening more—and that’s great. But you still need to assert something eventually, even if it's just, "I don't understand this." On the flip side, if you're someone who talks a lot, don't confuse that with authenticity. It’s not about being loud—it’s about being real and listening, too.
There’s no uniform outcome. It’s a pattern of thinking and interacting. It may require stepping a little outside of your comfort zone. But as long as you do it with the knowledge and confidence that comes from knowing what you’re talking about, it shouldn’t feel like you’re faking it. It should be coming, authentically, from you and your expertise.
I encourage people to stretch a little, but never perform a role.
This is great advice, but it can be daunting when everyone in the room, besides you, has years of experience. Do you have advice specifically for junior professionals? How can they establish their executive presence?
Joshua: One of the most overlooked advantages junior professionals have is proximity to execution. You may not be shaping high-level strategy yet, but you’re often closest to what’s really happening—what’s working, what’s not, and what’s unclear. Senior leaders aren’t always aware of those gaps. They’re not on the front lines, and they don’t always hear when things go off track. That’s where you come in. Speaking up about what you’re seeing, what’s difficult to execute, or even just saying, “I don’t understand how this strategy comes to life,” is not just okay—it’s essential. That’s something worth asserting.
But here’s the truth: it can be hard to do that in a culture that doesn’t value listening. If you’re in an environment where honest feedback from any level is dismissed or ignored, that’s a red flag. Culture matters. You don’t have to be in a place where everyone’s trained in the Ask and Assert model—but you do need people who are open to hearing others. If that doesn't exist, it may be worth rethinking where you are.
Still, even if you're not being heard right now, the internal work is valuable. Practice clarifying what you know, what you don't, what your instincts are telling you. Build that muscle. That way, when someone does listen—or when you find yourself in a better environment—you’ll be ready to speak with clarity and confidence.
That’s based on the idea that whoever you’re talking to will listen. What if you’re doing everything right, but they’re just not listening?
Joshua: It happens. Sometimes you need to talk to a colleague who has that person’s ear—someone who already has that trusted advisor status. Ask them to carry the message.
But also, be honest. If something doesn’t feel right, say so. Say, "I’m worried," or "I’m uncomfortable," or "I don’t think this will work."
When you’re up against someone who’s not listening, try to speak in terms they care about. If they value speed, say, "I think we’re going to lose time having to redo this later." If they care about risk, highlight what might be at stake.
Thanks for taking the time to answer these questions! Before we wrap up, I want to ask, do you have any other advice for younger professionals, or anyone early into their career, in this industry?
I’d just want to reiterate that it doesn’t matter how old you are, what you look like, what you sound like, or what your background is. These trusted advisor techniques are designed to be used by all kinds of people.
Because everyone has a truth to assert. And anyone can ask a smart question.
It’s like the marketing and communications equivalent of Ratatouille—“anyone can cook”. The same is true for being a trusted advisor. You just have to start experimenting with the ingredients!
Arden Reynolds is a Research Associate at Rob Roy Consulting, Inc.