Closing Time

A B2B’s Sellers Path to Becoming a Trusted Advisor (and Having Your Buyers Sell for You)

When your solution makes it on the agenda of your prospect’s weekly meeting, you’ve got a good chance of closing that deal. But how can you get your product or service considered at that level?

If you’re selling high-value deals involving multiple stakeholders, you’ll need a champion who trusts you.

Hannah Ajikawo joins Closing Time to share insights on building trust with your buyer champion and what questions to ask during the sales process to establish yourself as a trusted advisor. 

Trust is the currency of modern B2B selling, and becoming a trusted advisor in the eyes of your buyers is the ultimate gateway to long-term partnerships, enhanced credibility, and sales success. Find out how in this episode of Closing Time!

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Key Moments:
First step: Understanding your buyer's macro environment

In the world of B2B sales, closing deals isn’t just about showcasing your product or service; it’s about gaining a deeper understanding of your prospect’s world and helping them achieve their desired goals (ideally, with your product or solution). 

Hannah suggests beginning with the macro-environmental factors in your prospect’s business.

Then, narrow down your research from there.

Why should you start with the bigger picture? B2B sales often involve complex, multi-stakeholder decisions – on average 6-10, according to Gartner.

You want to prove early in the sales process that your solution is relevant to not just your champion but the company at large. This relevance makes it easier for them to see the value your product or service can bring to their organization and increases your chances of becoming an agenda item during their next team meeting. 

In your first few conversations with a buyer, ask about the most pressing issues in their industry or market. What are the recent changes or trends affecting their organization?

Dig deeper with questions like:

What organizational changes have they made in response to current trends?

When was the last time they reviewed a specific aspect of their business?

What internal disruptions or significant developments are they currently dealing with?

Hannah categorizes concerns into three buckets: issues (fundamental problems), challenges (obstacles to desired outcomes), and opportunities (areas for growth).

Once you have a strong understanding of the bigger picture, start to get more granular with your digging. Connect your champion’s role to the issues, challenges, and opportunities discussed.

How is your prospect’s role responsible for addressing the identified challenges? 

How have these concerns affected your prospect’s efficiency or processes? 

By engaging in these discussions and conducting your own research, you can start to instill the idea in your buyer’s mind that your main focus is not just selling your product, but guiding them towards a better future state.

* This is the beginning of your journey to becoming a trusted advisor. * 

Embracing the role of trusted advisor

To truly become a trusted advisor, your goal should be to establish trust and credibility right from the start of your interaction with a prospect.

The ultimate aim is to move beyond the traditional salesperson identity and position yourself as an indispensable resource.

Start to shift your mindset:

You are no longer serving your own interests; you’re serving your buyer’s interests. 

Salespeople focus on their products; trusted advisors focus on how their products can solve buyer’s problems. 

When you’re seen as the benchmark, prospects are more likely to turn to you for guidance.

The transition from salesperson to trusted advisor involves understanding your prospect’s situation comprehensively – just as a doctor asks about the symptoms, history, and desired outcomes before giving advice; you should gather essential information before proposing a solution.

Learn about the prospect’s current status, their past efforts or solutions, and their goals. By doing so, you position yourself as a credible source of guidance – someone who can offer direction and insights to help them achieve their objectives.

This shift in perspective, from merely selling something to genuinely advising and assisting, is what sets you apart as a trusted advisor in the eyes of your prospects.

Empowering buyers to champion your solution internally

As a sales rep, your role extends beyond the initial interactions with your prospect. It involves empowering them to become advocates for your solution within their organization.

Here’s how you can be “in the room without being in the room” and effectively guide buyers through this process:

Arming with Information: Provide your prospect with relevant perspectives, data-backed insights, and context about your solution. This empowers them to share your message confidently with their peers and stakeholders. They should feel like they have an earpiece, with you as the knowledgeable voice guiding them.

Building Trust: To gain your prospect’s trust, they must believe in your expertise. They’re risking their reputation by advocating for your solution. Be their go-to resource for any questions their internal team may have.

Supplying Resources: While there’s no fixed point to start supplying resources, it’s about anticipating needs. When your prospect is in the room, and discussions about your solution arise, help them foresee potential questions and challenges. Provide tools like white papers, blog posts, or structured information that equip them to handle these situations effectively.

Structuring Information: Think about how to present information that makes your prospect look knowledgeable and well-prepared. Help them anticipate what questions or objections might come up, and provide the answers and supporting evidence they need to assert the value of your solution.

Empowering your prospects to handle internal discussions confidently sets them up for success among their peers. This approach not only positions you as a trusted advisor but also increases the likelihood of your solution being championed effectively within their organization.

Remember, the goal is to be a valuable resource and partner to your prospect, even when you’re not physically in the room. By doing so, you create a powerful synergy that can significantly impact the success of your sales efforts.


If your prospect is bringing up your solution in their Monday meeting,
chances are you’re going to close the deal.
Let’s talk about getting on the agenda in this episode
of Closing Time.
Thanks for tuning into Closing Time the show for Go to Market Leaders.
I’m Val Riley, head of content and digital marketing at Insightly CRM.
Today, I’m joined by Hannah Ajikawo.
She is CEO of Revenue Funnel.
And a go to market strategy consultant.
Welcome to the show, Hannah. Hey, thanks for having me.
Ready to have some fun. Awesome.
I love the way you frame this, because in my day job here at Insightly,
we are both in the SaaS business and buyers of SaaS.
So I know that your opening statement rings true that if we’re talking
about buying a technology or a solution at our Monday meeting,
chances are we’re going to move forward with it.
Mm hmm.
No, I definitely say that.
And I think the the aim for reps and for teams is to really figure out
how do I make what I’m talking about
the most important thing in the world of this prospective buyer.
And it’s not that it’s easy, but it’s definitely possible.
And once we get to that stage, it’s about managing and keeping that momentum up
so that it can consistently on that agenda until they become a customer.
Let’s go through some tactics that you outlined
to get a mention or even an agenda item at that all important meeting.
The first is simply asking your prospects what are the biggest,
most pressing issues for them right now?
And so there’s so many different ways to frame this.
And the way that we don’t frame it is asking a prospect
what’s keeping you up at night.
I think it’s I think I don’t know who normalized that question,
but it’s one of the worst questions.
And I’ve said this before, but if you have children, I guarantee it’s your children
they say you reach a certain age in your life and your problems wake you up
and they could be anything.
I generally believe that we what we want to do is we always want to
look at the very, very big picture and all of the common trending themes,
all of the macro environments, and figure out for our prospect
how might that be impacting them both negatively and positively.
So I always look at three buckets, issues, so things that are fundamentally broken.
Challenges, obstacles or hurdles that stop you from reaching desired outcomes.
And opportunities.
So where you are trying to take advantage of something, trying to grow, to expand.
And we really want to look at the macro environment and say, okay,
what issues, challenges or opportunities might these these companies be facing?
And then we start to ask questions that tie into very critical priorities.
So it’s not what’s keeping you up at night, Val.
It’s really understand, Hey, like considering what’s going on in the world
today, what changes are you making in your organization?
When is the last time you reviewed this?
What is the thing that is creating the kind of
the biggest commotion internally, just something so you can get a gist for
what are people thinking about right now,
outside of AI, what are people thinking about right now?
So and that’s really what you want to do. So I’d say it’s
less of a tactic, but it’s this it’s almost like this character
you adopt where you’re like,. I really want to be someone
that can have a appear to be a conversation with you.
I love the way you kind of suggest a follow up question
because you’re asking them, Hey, what’s going on?
You know, in the business at the macro level?
And then your next question, the suggested question is,
and what is
going on personally in your role towards solving that issue?
So you’re kind of having them think big and then having them
think through the lens of their role in the organization?
Yeah, it’s not oftentimes that our prospects, that main person
or group of individuals that we speak to get the chance to take a step back
and then look back in at themselves and be like,
Oh, actually no, I didn’t see it that way.
But come to think about it, this is really tied to that thing
that that really big thing that’s happening at our organization,
which is global expansion or market share or product release, whatever it is,
and then they start to identify what role they play in that.
Because you have to understand, like if our solution
is on the Monday morning agenda, it has to fit with a broader narrative
or it’s value as some.
It’s not disrupting anybody else’s workflow.
There’s no horizontal application outside of this individual usage
and they can just pay for on their credit card.
But if it’s that big value, which is what we’re trying to go for, right,
we try to drive this big value, multi year, multi stakeholder engagement
that are really sticky.
It has to tie into something broader, something bigger
that is impactful inside the organization, particularly today, where people
just switch things off and say that’s fine. I’ll just subscribe to something else.
I do feel like just because of the way digital transformation is happening,
we’re forced to think of solutions not just as how they affect
one department or one team, but across teams.
And that’s where we’re getting into these
like buying committees that are seven, eight, nine, ten people.
Really, It’s organization wide, right?
But I love the idea of saying, hey, this is my role.
How does this impact my role?
And then having them think in terms of the broader organization.
Yeah, absolutely.
And I really want reps to figure out, like,
how do I get myself closer to those situations?
And it really is just understanding what’s valuable to people in any given time.
I always say like my accountant and people who sell accounting services
become really important to me towards the accounting end of year.
But when they’re prospecting me mid-year, I’m like go away.
But I’m hoping they contact me again because then I go
and try to chase them down.
So we have to also think about things like those seasonality,
what’s happening in their world, the time of year.
We know that that budgeting cycle period means that I have to
if it’s a big ticket sale that needs more eyes
and we should be doing that legwork and that research early on.
At what point does this need other eyes?
At what point does this go to RFP?
At what point is this X-Y-Z so that we can get in that budget
cycle and people can say, okay, you know, I’m looking at the big picture.
This is what I might need one of your tools or something similar.
I’m going to put that in and request a budget for that.
So there’s a lot of planning,
but we can only do that by understanding what’s valuable to people.
You know.
Just an understanding a prospect’s fiscal year could probably be
great information that sometimes we just aren’t privy to. But
just that one
variable, that one variable is how I used to plan out my entire year.
And I stuck to my outbound and my pipeline calls based on that.
And I kind of like lightweight prospecting.
I mean, this is a while ago, but my lightweight prospecting
to identify the right types of people, my company research,
I make sure that I understand when that company,
their financial year ended and that was it.
That was my personalization.
I understand that this time of year
you’re really thinking through the different types of tools and resources
you might need to hit outcomes in the coming year.
What’s front of mind?
How are you thinking about solving it?
Have you considered?
And people are like, No, thank you.
All right, let’s let’s have a chat.
But we don’t even get armed
with that oftentimes, we’re just guessing throughout the year.
So your next step, you say, is to become a trusted
advisor on the topic that has been identified.
If it’s in your wheelhouse great, right like that’s where you want to be.
Yeah. That’s really where you want to be.
Like, that’s
like for me, that’s the dream.
I’m like,. I want to as quickly as possible,
get rid of that identity of this salesperson.
I know people say, Oh, we know it’s sales.. Yeah, we know the people.
You know, I’m going to sell something to you and ideally make some money from it.
But what you want to do is establish trust and credibility so early on
with a prospect that they’re like,. I don’t even see you like the others.
I like, you are the benchmark and the others are like, What did they say?
But what did Hannah say?. What did they say?
But what did Hannah say? Like that that’s the kind of reference point.
I call it like creating a point of perspective.
So for me, a sales rep is like
someone that’s coming in to do what’s going to be best for them.
And because of that, we have thousands of different
data points that say people don’t want to speak to us, right?
And then we look at the trusted advisor, which is someone who a prospect
can look at as a sounding board, someone who can actually advise,
which is give me direction on the best course of action
that’s going to help me to achieve X,. Y, and Z.
You can’t do that if you firstly don’t know what direction they’re going in
and you also can’t do that if you don’t know where they’re at.
So we really have to understand if I’m going to advise you on anything
and I know people use the analogy of being in a doctor’s
surgery, but it’s always going to be like,. When did this start?
What have you done so far?
What have you taken, What have you tried,. How long has it been going on?
And then where are you trying to get to? It’s just
and that is the thing that starts to establish you as a trusted advisor.
You are in a position of authority when it comes to the information
that you can provide to someone.
So you know, a little bit more than them or can at least shift their perspective.
So tell me what you mean when you say being in the room
without being in the room,
because it sounds like that’s part of that trusted advisor role.
Yeah, that’s a big part.
And again,
we are not in the room for the majority of most sales engagements.
It’s just how it is.
So there’s a lot of learning, independent understanding that happens without us.
And we have to sometimes play catch up.
Okay, so what happened?. Tell me what happened in that meeting.
Tell me what they said.
What was the email exchanges?
So so being in the room about being in the room is essentially arming
our prospects with the perspectives, the data backed,
you know, context backed based on what they’re going through, relevant
so that they are almost doing your job with confidence.
And what they’re doing is they’re feeding back what that response
looks like and saying, Hey, Hannah, what do I do next?
This is what they said, What do I do next?
And it’s like, I don’t know if you watch like CSI, but it’s like the ear piece.
It’s like that ear piece and they’ve got a wire on and you’re that person.
But they need to be, they need to trust you
to risk their reputation internally with their own stakeholders
and peers in order to say, I’m going to listen to what Hannah’s saying
and advising, and I’m going to deliver that to my team like it’s my own ideas.
So at
what point do you feel like it’s like supplying actual resources
appropriate like, white papers, blog posts, etc., or is this more about
just kind of at
this point, just listening and reflecting at this stage of the sale?
I don’t think there’s a right point.
As in like this is when I should start.
It’s more a case of flipping,
flipping the mindset slightly to when that person is now in the room
and they say, Hey, let’s use Insightly as an example.
I I’m thinking about Insightly CRM to do these things.
Now I feel like we’ve matured to a stage now where we need a platform
that’s a bit more robust and everyone’s like insightly of,
you know,. I saw some marketing material, okay?
And they’re like, look,
But then they’re going to have three or four or five or six questions.
It’s at that point that you say to yourself, I’m not in the room.
What do I think these people are going to ask?
What do I think they’re going to be thinking about?
What challenges or kickbacks may they be?
Now, this isn’t the battle cards.
The battle card is all right for you some call training, but this is really
how do I structure this information that makes this prospect think, oh,
my God, I’m not going to embarrass myself because I have no idea.
I don’t know. I’ll come back to you.
Yeah. Okay. Yeah. So, yeah, this is what.
This is what it does. This is how it’s different from other platforms.
This is why it’s better.
So they’re in that position of power.
So I think it’s more a case of just understanding those next two
or three steps and then arming the prospect with those tools to say,
if you need them, they’re ready.
But I think these things might come up.
And that’s perfect.
You’ve put them in a position to be successful among their peers.
You’ve put yourself in a position to be that trusted advisor
and you know, that’s where the magic happens, right?
Yeah, exactly that, exactly that.
And I really think you start to establish trusted advisor status when you can drop,
you start the drop formalities, you start to
you don’t have to keep saying I hope you well you just like you know
it’s shorthand, it’s free, it’s it’s. WhatsApp, it’s text message,
it’s a two second call.
It’s forgetting something and being able to quickly
pick up the phone and say, Hey,. I just forgot something in our meeting.
Can we still do X, Y, and Z?
It’s asking for favors both ways and you just know.
You just know, even if it’s really, really early on in the sales engagement.
I mean that’s just where everybody wants to be right, Hannah.
Awesome. Well, that’s all the time we have for today.
Thanks for taking us on that journey.
It was extremely helpful. You’re welcome.
Thanks for having me.
All right.
And thanks to you all for tuning in to Closing Time.
Be sure to like this video,
subscribe to the channel and ring the bell for notifications
so you don’t miss an episode.
We’ll see you next week on Closing Time.

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