This article is by Hiten Shah, co-founder of three SaaS companies: KISSmetrics, Crazy Egg and, most recently, Quick Sprout. He's an angel investor and advisor to more than 50 companies. Here, he shares why context is the most integral part of giving advice — and how to surface it faster and better.
"Hey, you're f*cking up, and here's why. Let me show you what the opposite of that looks like."
Those two sentences introduced the best advice I’ve ever received. Not only did it change the course of my company at the time, but how I approach giving advice, which I do three times daily on average — and sometimes up to eight times a day.
When I was told those words, I was a few years into KISSmetrics. The startup was stabilizing after a lawsuit. It had taken six months to regain our footing and return to thinking about the business. Still a bit shell-shocked, we were sending weekly updates to our investors. One of them, a CEO of a public company, reached out: “I need to meet with you within the week.”
There were no opening pleasantries. He got into the meat of it, telling me that I wasn’t thinking of the company as a business. I was running a SaaS startup and making subscription revenue, but wasn’t looking at it the right way in his mind. “Here,” he looked me in the eye, “let me show you an example from someone we both know who’s doing it right.”
He laid out the ideas so cohesively that it felt like a polished board deck. He cussed, but wasn’t disrespectful. He spoke with intelligence and intolerance. “Here’s how they think of these three areas. Boom, boom, boom. What are you waiting for? See how you can look at your company differently?” I told him I got it. Before I knew it, I was walking out of his office.
It was a revelation for me — honestly a company- and life-altering experience. Yet from this account, it may not be apparent why. It’s because 90% of what made his advice so effective was not the counsel itself — but the context in which he couched it. The impact came from his anticipation, actions and approach as much or more than the actual answer. Here’s how he did it — and how I’ve learned to do it:
Convey importance with the irregular. Most people casually offer an opinion masked as well-considered advice. It’s no wonder that it’s so hard to separate the signal from noise. In this case, before a substantial word was uttered, he signaled that this time was different. He changed his behavior, which got my attention and instilled gravitas. He knew that I know that he rarely wants to meet up; it just isn’t his thing. Normally I’d email him, he’d triage the request and the right person would get it done.
The second byproduct of the in-person meeting was that he demonstrated change before he expected me to alter my ways. Of course, the degree was different: his adjustment was in how he met with me and mine would be about how I ran the company, but the symbolism was there. I knew he didn’t prefer to meet that way. Because he was willing to change his habits to help me — even in a subtle way — so was I.
After some diligence, be direct in every way. He had been reading the investor updates, related to my situation as CEO and knew that I didn’t often ask for advice from others. So he did a lot of processing before reaching out. Once he did, he used every trick in his book to cut to the heart of the matter: He demanded to see me within the week. He swore in order to emphasize a point and firmly grab my attention. He wanted the meeting to be in-person, so I would take in every inflection of his voice or microgesture.
The CEO didn’t just speak directly — he made sure everything about the conversation embodied the level of unswerving honesty that he knew I needed. Then he leveled with me: “I saw it, so had to say it." That idea stuck with me. He didn’t hold back because he knew I had something to learn and there was no reason to wait. You know how some people can’t hold their tongues? We both are the type of advisors who can’t hold our throats. Even if it’s that far back, we can’t keep it from rising to the surface. He was a representation of something that I really valued: the ability to be direct in every dimension — not just speak directly.
Use shared context to resonate, not just relate. The most powerful technique that he used was framing my problem in shared terms that resonated for both of us, but belonged to neither of us. Here’s what I mean: when he raised the example of the company that was doing it better, he purposely chose an example that we both knew — and had observed and could instinctively vet — but that wasn’t just from one of our pasts, which might be prone to misinterpretation or bias. Not only did I know the company he referenced, but I was one of its advisors.
I’ve learned that if you’re asked about your past, only bring it up if you’ve made sure it’ll be helpful to others. Too often those examples are for the advice giver, who either shares to relate or assumes that her own context is sufficient as counsel. It’s a dangerous trap. It’s much more valuable to examine a context familiar to both of you. That shared reference point allows both the advice giver and receiver to use an informed, common language, but the distance from both parties allows them to think critically and more objectively about the situation.
To get immediate relief, focus on the advice. If you seek wholesale change, hone in on the context of the advice.
Does that sound like a lot of work? Maybe, but it should be. Especially for the kind of advice that may alter the trajectory of a product, founder or company. That’s why I don’t often seek advice. I ask for candid feedback, additional information, more data — that’s a whole different story.
In the rare moments when I ask for advice, I look for someone who can help me think about a problem in a way that I haven’t considered. Only when I’m truly looking for a change do I consider soliciting advice. In the case of my investor, he saw the signals even when I didn’t — our slow return to the business post-lawsuit plus the content and cadence of my board updates — and knew my patterns well enough to shake me into action. This was a rare, profound case.
In the end, an effective exchange of advice is specific to the giver and receiver of the counsel. Yet, like any human interaction, there are general patterns for those who want to get better and faster at soliciting and giving advice. The best advice givers not only see the patterns, but also pick and choose which ones makes sense for the situation. If you’re advising, here are three ways to surface the right patterns; if you’re seeking advice, listen to those who do the following:
Jumpstart recognition through research.
It’s common practice to do research before meeting with a person, pitching a company or entering a market. Similarly, it’s critical to research the people to whom you may give advice or for whom you may receive it. In these cases, it’s less to gather information — though helpful — and more to jumpstart the recognition of patterns.
Yet, if you frequently give or ask for advice, you might say you don’t have the time to kickstart identifying patterns before advising. Here’s a few ways how, for both 1:1 and group sessions:
- Choose a video over words. If you only have time to view a video clip or an article featuring the advisor or advisee, opt for the former. Many of my fellow founders and friends will watch videos of people before they meet them because video provides multidimensional input. They not only hear the content, but also take in posture, gestures and intonation. Even a short video clip — or audio, as a second option — can put you on better footing and give you greater context before an exchange of advice.
- Listen at 2x speed. This tip is more of a productivity hack to increase your daily consumption of information, but it applies here. Listen to an audio clip of them talking in double time. You’ll be surprised how quickly you adjust to the speed and absorb information about them.
- Integrate up-to-the moment interactions. This mainly applies to settings in which advice is imparted from one to many. If asked to speak at conferences, I like to go on stage later in the day than earlier. That way I can sit there, listen to the audience’s questions and refine my deck accordingly. Sometimes I’ll include quotes from the other presenters. Not only does this allow me to know where to start my talk or advice, but to more quickly level up the information that I share.
- Round-up introductions. I know I have a harder time in group settings where the goal is to exchange know-how and advice. It’s a challenge to get context in those settings. I counteract that by making people introduce themselves — even if the group is up to 50 people. It’s that important. It’s the most valuable part of the session because it allows me to know who’s in the room and how they think about their work. If you’re advising just one person, ask her to introduce herself for the same reason. Try it even if you know them well.
Ask questions about growth, not motivation.
If you asked my KISSmetrics investor about the reason why he gave me the advice, it’s because he wanted me to get better. He never said that, but he oriented all of our conversations around growth. His questions helped me clarify how I was going to do it, more than why.
I understand the value of starting with why, but when you’re at the threshold of asking advice, you should already have that answer. You should be on the verge of acting, but may not know how. At that point, it should be less about your motivations to act, but your method of doing so.
In my account, both the CEO and I had led enough companies to know that the motivations for growing them will change. Sometimes it’s for influence, ambition, a podium, camaraderie, energy — the list goes on. In the end, that shifts and is subjective. What isn’t is growth.
The very simple way to reroute a conversation to growth is reframing the questions that you ask or that are asked of you. As I've mentioned before, I often get these questions:
- When you started KISSmetrics how did you start your blog?
- When you hired your first salesperson where did you find them?
- When you raised your first round of funding how did you do it?
What I ask in response are these questions:
- Are you trying to figure out how you should do marketing for your business?
- Are you starting a sales team and trying to hire the first person?
- Are you thinking about raising money for your company?
This would have been a better line of inquiry to start:
- I’m figuring out how to do marketing for my business. What should I be thinking about?
- I’m starting a sales team and trying to hire the first person. How should I approach it?
- I’m thinking about raising money. Where should I start?
This would have been their best line of inquiry to start:
- I’m figuring out how to do marketing for my business. Here’s what we’ve tried out and these are the few tests we’ve found to work for us. What should I be thinking about next?
- I’m starting a sales team and trying to hire the first person. Here is who our target customer is, our average revenue per customer and what our sales process looks like. How should I approach it next?
- I’m thinking about raising money. I raised my seed six months ago led by this firm, it seems the profile of this partner is the best fit and these are the reasons we’re raising a round right now. What should I do next?
There are a few key takeaways in the evolution of these lines of inquiry:
- Favor questions with verbs in the present participle versus those in the past tense. Using “ing” verbs roots the advice giver and receiver in what’s currently in motion — and can be acted upon. Asking about what either party did should be brief as context, secondary and teased out through the conversation if necessary.
- Reframe questions to orient around the advice seeker. The advice giver will naturally bring her experience into her answer, but it shouldn’t be in the opening gambit or focal point. Anchor the conversation in the present and allow the advice giver’s experience to surface in the follow-up questions she asks.
- Provide context like a constellation. The difference between the good and best line of advice-seeking is pithily providing a spread of data points between which the advice giver can draw the lines. This data rapidly signals to the best advice-givers where you are in the process, the questions you’ve likely asked — and haven’t asked — and your understanding of where you are. It also accelerates the conversation by cutting the pretense and quickly placing both parties on the same page.
- Ask what you should do next. Any good advice should lead directly to action. Asking for counsel on what you should do next transmits to the advice giver that you a) both understand where in the process the advice seeker stands, b) brought the advice giver in at the right time — and aren’t wasting her time and, most importantly, c) are ready to take an immediate and concrete action.
All good advice tips people toward action, not options. You may think all you need is advice. Practice is what you need.
Reserve judgment.
This may be the most straightforward of all tactics, but the hardest to master. Good advice takes pattern recognition and selection, but with that, comes the tendency to rigidly categorize people alongside their situations.
So here’s the mantra of the advice giver: don’t react. Ask yourself how to advise in a way where you’re not judging, so others will remain open to what you’re going to say. That starts with you being open to what they’re saying, too.
I’ve been asked to advise and speak on a number of areas, ranging from enterprise sales to fundraising. The truth is that I actually really dislike some of these topics. Some people may know what they are, but I mostly don’t tell people. That’s because advising is not about me.
So, if diving into that topic is the right thing for your business and you’ve asked me about it, I’ll tell you about it and we’ll work through the problem. Some of the highest praise that I’ve received after giving advice has been in areas that I wouldn’t have elected to talk about if given the choice. But I’ve needed to reserve my judgment because others have requested that counsel.
We’re in the early stages of building Quick Sprout and it can feel like a long ramp-up to launch, especially for founders who have done it before. I felt antsy and my chops felt rusty; I realized that I needed to launch. So I decided to design and ship a silly t-shirt.
I’d never done something like that before and needed advice. I received it from a very savvy, talented teenage founder. When I was ready, I asked him for counsel on promotion and sales for the shirt and he helped me think through how I’d execute in specific, concrete ways. Some may not take to being advised by someone half their age, but that’s exactly why you must continuously withhold judgment. In the end, I wanted his perspective, involvement and an opportunity to learn.
A growth mindset: that’s what it really boils down to. If you’re getting my advice, it’s because you want to learn.
You may have noticed that I never mentioned the names of the KISSmetrics investor or the teenager. It’s because it doesn’t ultimately matter. One’s well known; the other less so. One has led companies longer than the other’s been alive. Yet the critical commonality is that they both took time to understand my context — before, during and beyond our meeting. They invested in learning my patterns, provided direct advice, geared the conversation in terms of growth and reserved judgment until I finalized my plan to act.
Here’s what I know: in most cases where advice has its greatest impact, the work begins with the advice seeker. If that’s you, take time to investigate where you need help in your business before asking for it. Don’t settle and immediately ask others about their past experiences. Dig into where you need to grow next. Start with your business fundamentals. That sounds basic, but I’m constantly surprised how many people forget it. They point to bubbles and unicorns instead. The source is your business and yourself. The great advice and progress soon follows.