HBR: A Guide to Cold Emailing

Have you ever used email for cold calling? If not, this article may be useful to learn how to use email to attract new clients. Below is a blog from the Harvard Business Review by Tucker Max.

A Guide to Cold Emailing

Cold emailing is harder than most communication for two reasons. You have no relationship with your audience yet, and you lack non-verbal feedback, so you can’t modify your approach in real time. As a result, most cold emails fail.

But they can work well. People have built careers and launched start-ups with little more than cold emails. (By the way, I am not talking about sales emails, which tend to be sent in bulk. This article is about cold emailing a specific person.)

There isn’t much research on cold email, though Shane Snow did an interesting experiment for his book Smartcuts. He sent 1,000 cold emails to executives and got almost no response. So he tried again with a smaller slice of the same group and got better results by applying a few principles that line up with my extensive cold email experience and some great advice from people like Wharton psychology professor Adam Grant, and entrepreneurs Tim Ferriss and Heather Morgan.

An effective cold email does five things. It should:

  1. Tailor the message to the recipient. You need to do your research. But there’s a right way and a wrong way to do that.

I’ve received about 25,000 cold emails since 2004 (yes, I do keep track). Many of them make a generic mention of something on the first page of Google results for my name, then launch into a ridiculous, tone-deaf request, like “Hey, can you read my 300-page novel, give me extensive notes, and then get me an agent?” That is not personalization.

Personalization means that you’ve thought about who this person is, how they see the world, what interests them, and what they want — you’ve developed a “theory of mind” about the recipient. This shows them you have put work into understanding them.

You also make it clear why you are emailing them as opposed to anyone else. Research shows that people are far more motivated to help others when they feel uniquely qualified to do so. By outlining precisely where they fit in, you can tell a story that makes sense to them.

It’s also important to make sure your request isn’t easily fulfilled another way. I cannot tell you how many emails I get asking for advice on how to write a book, even though I literally wrote a book on that exact subject. Through personalization, you avoid that, because you’ve read up — you know the book’s out there.

  1. Validate yourself. When we meet a stranger or get an email from one, we want to know who that person is and why that person matters to us.

Remember that when you’re the stranger. You’ve already done a bunch of research on the people you’re emailing, but they don’t know anything about you. You need to show them you’re credible and they can trust you.

Knowing someone in common is the strongest form of social proof you can offer. If you have any direct connections, mention them. A mutual friend means you are no longer a stranger.

Lacking that, if you have any authority, credibility, or social status that is relevant to this person and your request, mention it quickly — a line or two should do it. The more “important” you are, the more likely you are to get a response.

If you have no real status, that’s fine. Find a commonality. Being part of the same group, especially if it’s a personal group, is a core human attraction. Look for unexpected connections, like hometowns and unusual hobbies. As Adam Grant points out, “Similarities matter most when they’re rare. We bond when we share uncommon commonalities, which allow us to feel that we fit in and stand out at the same time.”

The point is, you want to find a way to go from “stranger” to part of the recipient’s group.

  1. Alleviate your audience’s pain or give them something they want. Why should the recipient care about your email? Why should this busy person take time to respond to it? What’s in it for them?

Remember that people will go much further to avoid pain than to acquire pleasure. If you’ve done your research and found a major pain point for the recipient, and you can offer relief, highlight that. Consider this example: A VC friend of mine once complained on Twitter about how his car was constantly getting tickets because the street signs were misleading. An entrepreneur looking to pitch his start-up started his cold email with a link to a robo-calling service that took care of parking tickets. The VC used the service and was so thankful that he not only took a pitch meeting but also connected the entrepreneur to several other VCs, two of whom ended up investing.

If you can’t solve a problem, give people something they want. Offer to connect them with someone they’d like to meet — that stands out, since almost no one gives before they ask. But your gift needs to feel appropriate, from one stranger to another. An Amazon gift card would be super awkward and weird. I know, because someone sent one to me once.

  1. Keep it short, easy, and actionable. The opportunity to help someone is very enjoyable for a lot of people — it may even qualify as a “want.” By asking for help, you are giving them the chance to feel good about themselves. But make it easy for them.

You probably know this, but short emails are more likely to be read than long ones. And emails that request clear, specific action get a much higher response rate. Long-winded, rambling cold emails suck.

One of the best ways to keep things short and direct is to write the way you’d talk. If you met this person at a cocktail party, you wouldn’t just walk up and start pitching them. You’d introduce yourself, say something nice, connect with them over a shared friend or interest, and then make a request that makes sense.

I would recommend reading your email out loud before you send it. If it sounds natural, then it will read well. This is how I edit my own writing.

To make your “ask” easy and actionable, do as much work for your audience as you can. “Let me know if you want to meet up” is terrible. This forces someone to exert mental energy to make a decision for both of you, and it puts the onus on them to sort out the details. It’s short, but not easy or actionable.

Compare that with this: “I can meet on Monday or Tuesday between 8 a.m. and 11 a.m. at Compass Coffee on 8th. If that doesn’t work, tell me what does, and I’ll make it happen.” That gives them a clear, easy action to take, with specific bounded options.

But there’s more to a good “ask” than just telling people what you want. How you tell them matters a lot.

  1. Be appreciative — and a little vulnerable. I would even go so far as to say you should be slightly submissive.

I’m not saying to grovel before your audience like they’re a feudal lord. You are asking someone who does not know you for a favor. By expressing gratitude and some vulnerability, you give them the feeling that they are a good person if they choose to help. You also give them a little rush of power and status, because you’re approaching them.

This gets results. Even just saying “Thank you so much! I am really grateful” to a request doubles response rates. And tell people it’s fine if they are too busy. Giving them a way out actually makes them more likely to help you.

All this may sound obvious, but again, very few people do it. I’d say about half the people who have cold emailed me expressed no appreciation beyond a perfunctory “thanks.” And the other half either sounded brusque or entitled. Really — strangers asking for huge favors say things like “Lemme know how quickly I can expect you to get this done.” Clearly, they don’t feel like waiting around. But that tone has repercussions: I don’t feel like helping them.

Finally, don’t use a template. If you Google “cold email template” you will find a LOT of them. I looked through dozens, and though some were very good for mass email and sales, I could not find a good template for a personalized cold email.

Which makes sense. By definition, if something is personalized, it doesn’t come from a template. That’s why this article lays out principles but has no scripts.

I did find some good examples of cold emails (this one, for instance, and this one), with breakdowns of how and why they worked. You’ll notice they each used almost every principle here.

 

FOCUS: How Gritty Leaders Articulate Purpose

The Four Virtues of a Leader: Navigating the Hero’s Journey Through Risk to Results by Eric Kaufmann is a quick and enjoyable read. He talks about four key questions to keep you on track: What am I creating? What am I avoiding? What am I sustaining? What am I yielding? Below is an excerpt from the book:

FOCUSFour Virtues.jpg

Purpose is the focusing element we need to understand and develop among the building blocks of grit. Grit is a forward-facing principle. Running away from something isn’t grit; it’s fear. While fear provides a strong motivation to keep running and moving, it drives you from behind as it pushes you along. Grit, on the other hand, magnetizes you toward a long-term objective. Clarity of purpose is a critical element for successfully developing and enhancing your grittiness; this can be something as broad as your life purpose, or a more narrowly defined sense of purpose for your work, team, or project.

Purpose draws from your focus, from your answer to “What am I creating?” In formulating your focus, you keep attention toward the horizon, and in so doing forward becomes obvious and easy to press toward. Leadership is a constant vigilance toward the future, toward what’s coming, as well as to the present, to what’s happening now. Long-term goals feed grit. We persevere when the future plays an active role in moment-to-moment decision making.

I’ve seen a common pattern among people who are most effective at remaining on purpose. I’ve coined the acronym FOCUS as a thinking guide that reflects how gritty leaders articulate purpose. FOCUS is a way to concentrate your efforts forward and bring forth the elements that empower grit:

F-Fulfilling. Is your goal fulfilling to you? How does this long-term goal feed your spirit? How does it make you a better person? Beyond the things that we have to do that we find challenging and difficult, how is this work feeding your soul? My job is challenging. It takes lots of attention and energy. Yet I grow and learn and make extremely rich and meaningful connections. I can press through the challenges because my work is fulfilling. My grit-my perseverance for striving to improve professionally-is fed by the fulfillment of being of service, of touching people’s lives in a meaningful way.

O-Optimistic. My daughter has a glass on her desk half filled with water. She keeps it there because she wants to be gritty, and gritty folks choose to look at the glass as half full. It’s difficult to be gritty when you’re pessimistic about your goal in particular or future in general. You can learn and practice optimism, and the optimistic aspect of FOCUS isn’t just looking at the world positively, but looking forward and being engaged by the future. Being focused on the goal means that you direct yourself toward it; being optimistic about your goal means that you look forward to it. It’s nearly impossible to persevere toward something that you dread.

C-Challenging. Believe it or not, if the purpose is too easy or too ordinary, we lose interest in it. It’s paradoxical that grit-stamina and determination in the face of difficulty-is activated by the very presence of challenge and difficulty. Being challenged has a stimulating and energizing effect when the goal is also fulfilling; you strengthen grit when you know that you’re working toward something fulfilling and challenging.

U-Urgent. To stay on track with your purpose, it has to entail a sense of urgency. Urgency keeps your intention top of mind and your attention focused. This might sound counterintuitive, as grit refers to passion and perseverance for long-term goals. Yet if the long-term goal has no sense of urgency, then it simply languishes in the “would-be-nice-someday” category. When urgency turns to stress, though, it actually consumes the ability to be gritty. What builds purpose for true grit is your continued attention to the urgency of the goal while maintaining a rational detachment from the strain and stress of the deadline.

S-Specific. The final component of FOCUS is that the goal is specific; it’s restricted. During strategic planning, I refer to strategy as the “art of exclusion.” Being specific means honing in on one defined outcome and ignoring the other possibilities and temptations. Losing weight through diet and exercise can take a while, often longer than we wish, and saying, “I want to lose weight” is fairly useless. But saying “I want to weigh 140 pounds” is specific. “Hiring good talent” is vague; “hiring three experienced trainers” is specific.

SMART Goals

The practice of goal-setting is helpful in the pursuit of happiness. Psychologists tell us that people who make consistent progress toward meaningful goals live happier, more satisfied lives.

If you don’t have written goals, I encourage you to make an appointment on your calendar to work on them. You can get a rough draft done in as little as an hour or two. Few things in life pay such rich dividends for such a modest investment.

A SMART goal is an acronym for achieving your commitments. Below are the five meanings:

  • Specific—Your goals must identify exactly what you want to accomplish in as much specificity as you can muster.
  • Measurable—If possible, try to quantify the result. You want to know absolutely, positively whether or not you hit the goal.
  • Actionable—Every goal should start with an action verb (accomplish, organize, increase, develop, budget, etc.) rather than a to-be verb (am, be, have, etc.)
  • Realistic—A good goal should stretch you, but you have to add a dose of common sense. Go right up to the edge of your comfort zone and then step over it.
  • Time-bound—Every goal needs a date associated with Make sure that every goal ends with a “by when” date.[1]

Your next steps are as follows:

  1. Write them down. This is critical. There is huge power in writing down your goals.
  2. Review them frequently. Writing your goals down makes them real but the key is to review them on a regular basis and break them down into actionable tasks.
  3. Share them selectively. Sharing them with those that are important to you and someone to whom you can be accountable.

[1] Michael Hyatt and Daniel Harkavy, Living forward : a proven plan to stop drifting and get the life you want (Baker Books, 2016), 95

HBR: Developing Employees’ Strengths Boosts Sales, Profit, and Engagement

As a manager or owner, are you focusing on your employee strengths? What are you doing to strengthen your employees’ performance? Below is a blog from the Harvard Business Review by Jim Asplund and Brandon Rigoni, Ph.D.

Developing Employees’ Strengths Boosts Sales, Profit, and Engagement

Should companies primarily focus on playing to the strengths of their employees or help them improve on their weaknesses? This question is particularly important today, given low workplace engagement and higher expectations from workers about what a great job entails.

Gallup has studied thousands of work teams and millions of leaders, managers, and employees for more than five decades. We’ve found that there’s significant potential in developing what is innately right with people versus trying to fix what’s wrong with them.

We know, for example, that the more hours a day adults believe they use their strengths, the more likely they are to report having ample energy, feeling well-rested, being happy, smiling or laughing a lot, learning something interesting, and being treated with respect. In addition, people who use their strengths every day are more than three times more likely to report having an excellent quality of life and six times more likely to be engaged at work.

Focusing on employees’ strengths does more than engage workers and enrich their lives, however: It also makes good business sense. Gallup recently completed a large study of companies that have implemented strengths-based management practices. The companies we studied develop what comes most naturally to people — e.g., having employees complete the CliftonStrengths assessment, incorporating strengths-based developmental coaching, positioning employees to do more of what they do best every day, and the like.

The study examined the effects those interventions had on workgroup performance. It included 49,495 business units with 1.2 million employees across 22 organizations in seven industries and 45 countries. Gallup focused on six outcomes: sales, profit, customer engagement, turnover, employee engagement, and safety.

On average, workgroups that received a strengths intervention improved on all of these measures by a significant amount compared with control groups that received less-intensive interventions or none at all. Ninety percent of the workgroups that implemented a strengths intervention of any magnitude saw performance increases at or above the ranges shown below. Even at the low end, these are impressive gains.

  • 10%-19% increase in sales
  • 14%-29% increase in profit
  • 3%-7% increase in customer engagement
  • 9%-15% increase in engaged employees
  • 6- to 16-point decrease in turnover (in low-turnover organizations)
  • 26- to 72-point decrease in turnover (in high-turnover organizations)
  • 22%-59% decrease in safety incidents

So how can your organization approach these impressive numbers? This research, combined with our work with hundreds of organizations, also identified seven best practices for optimizing strengths initiatives. Companies that practiced more of them saw results at the top of the ranges shown above.

Start with leadership. Sometimes a few isolated departments will implement strengths interventions independently, creating a limited impact. But when leaders make these interventions a fundamental strategic priority, that’s when change really happens. Take profitability, for example: We found that the potential for increased profits multiplies when top-level leaders push strengths throughout the entire company.

After a four-way merger, senior leaders at a North American company implemented a “Lead With Your Strengths” program to help employees at all levels understand how to use their strengths to navigate the change, and to foster a unified culture with a shared operating strategy and mutual goals. In the first year alone, the company’s employee engagement levels improved by 26 percentile points in Gallup’s overall organization-level database.

Get managers on board. The best way for employers to maximize workers’ strengths is through their managers. Almost seven in 10 employees who strongly agree that their manager focuses on their strengths or positive characteristics are engaged. When employees strongly disagree with this statement, the percentage of engaged employees plummets to 1%. Manager alignment on a strengths initiative is crucial because managers are ultimately responsible for developing workers based on strengths. This best practice has a profound impact on performance.

Generate awareness and enthusiasm company-wide. When strengths concepts are consistently communicated, employees use their strengths more. A mid-sized financial services company prominently displayed each employee’s top five strengths in their office or cubicle — helping all employees keep one another’s natural talents top of mind. Leaders should also communicate their business strategy in terms of their organization’s competitive strong points – their company’s strengths. Additionally, they need to deliver praise throughout the organization in ways that convey how individuals and teams within have relied on their strengths to be successful. These messages encourage everyone to buy in.

Be mindful of strengths when creating project teams. Not only do leaders need to create ways for all employees to increase their self-awareness, but they should also employ tactics to ensure teams are assembled with each individual’s innate talents in mind. Responsibilities need to be assigned based on what comes most naturally for each team member. For example, strategically partnering two people — whereby both contribute in their area of greatest strength — can make the difference between whether or not teams accomplish overall goals, or even simple objectives.

Focus performance reviews on the recognition and development of employees’ strengths. Even leaders and managers who are motivated to capitalize on their employees’ strengths will find this difficult to do if the company’s performance management philosophy focuses on fixing employees’ weaknesses. A strengths-based approach to performance management is straightforward, appealing and decisive. Managers should conduct performance reviews that encourage and make use of employees’ talents and offer recognition and development aligned with their strengths. Managers should also provide clear performance expectations and help workers set demanding achievable goals. One result of strengths-based performance management is that employees feel their manager knows and respects them, which in turn boosts their performance.

Build a network of strengths experts and advocates. A company’s internal strengths advocates and champions are personnel who play a crucial role in supporting all employees in using what they’re good at to the best of their advantage. These champions help drive the strengths movement at every stage, from initial launch efforts to sustaining momentum down the road. Ultimately, their consistent encouragement can propel the company to world-class performance. One investment management company in the U.K. grew quickly with a network of internal experts who helped employees understand how they could use their strengths more effectively. The result? Despite a competitive and changing market conditions, these individuals were able to adapt to constantly changing environments and develop their skills at the same time.

Tie the organization’s strengths-based culture to its larger brand. A brand that reflects an organization’s strengths-based culture goes a long way for the company. A strengths-based brand attracts the right kind of job seekers – those who are driven to apply and develop their strengths and would be a good fit with the organization’s culture. A strengths-centric brand is also compelling to customers, which can differentiate a company from the competition.

Struggling to live up to its brand promise of exceptional customer service, a large retail company trained its employees to offer shoppers personalized knowledge and advice about purchases, installations, and repairs. When employees were also encouraged to understand and use their strengths, they did an even better job of connecting with customers and providing individualized service. Stores that implemented the new customer strategy and the strengths-based focus grew 66% faster than stores that didn’t use strengths in the initiative.

Now, let’s be honest: employees can’t completely avoid their weaknesses. That just isn’t possible in the real world. But instead of having people waste too much time trying to improve in areas where they’re unlikely to succeed, managers can form strategic partnerships and thoughtful processes that help them work around their weaknesses. Our data suggest that focusing energy on improving in areas that come most naturally to people reaps high returns, as employees and organizations that incorporate strengths as a strategy tend to realize significantly positive business results.

 

Detroit Hustle

 

This memoir is a quick read; Detroit Hustle: A Memoir of Love, Life & Home by Amy Haimerl. She writes about her dad’s advice on contractors. Below is an excerpt from the book:

Detroit HustleDetroit Hustle.jpg

Contractors, he said, have a right to feed their families. Don’t look for cheap; seek quality work at a fair price. That is so important that Dad had this bit of philosophy inscribed on the back of his Bear Excavating business cards: “The bitterness of poor quality and workmanship remains long after the sweetness of the low bid is forgotten.” I remember reading that as a kid, and it’s always stuck with me. Be direct and decisive, he added. Know your budget and be honest about it. Pay on time. Look for someone who is a partner, who asks good questions and seems to care about the answers. Look for someone who can make suggestions and offer alternatives. Go with your gut and understand that your contractor is worth every dime because that’s the person who will make the project either a dream or a nightmare. You’re going to be more married to them, he tells me, than to Karl. Finally, make sure they are bonded and insured

HBR: The Best Salespeople Do What the Best Brands Do

Does your sales force create extraordinary experiences that embody your company’s brand?  Are you cultivating emotional connections with customers and providing real value for them? Below is a blog from the Harvard Business Review by Denise Lee Yohn.

The Best Salespeople Do What the Best Brands Do

It’s not news that the role of salespeople and selling is changing. In the past, salespeople were often the first step in a purchase process, and could significantly influence customer decision-making by controlling information about pricing, availability, competitive advantage, etc.

But in this era of nearly ubiquitous information, customers usually engage with salespeople after they’ve already researched their purchase and in some cases made their purchase decision. Digital commerce and disintermediation have caused many customers to question the importance of having a sales relationship at all. Moreover, companies are learning that true sales success isn’t indicated by the number or size of deals closed; it’s measured by getting and keeping the right customers.

Great salespeople succeed in this new business environment by doing what great brands do. I laid out seven critical brand-building principles that great brands follow when I wrote my first book. I’ve now found that these principles are as instrumental to restoring sales to its role as a valuable, sustainable, integral business function as they are to building great brands.

  • Great brands start inside. Great salespeople sell inside first. Just as great brands start brand-building by cultivating a strong brand-led culture inside their organizations, great salespeople know the first step to sales success is actually one taken inside their own companies. They contribute tremendous value to their organizations through their market insights and direct communication channel with customers. So they help their companies with product development, marketing strategy, and customer service by serving as the Voice of the Customer internally.
  • Great brands avoid selling products. Great salespeople cultivate emotional connections with customers. In the book What Clients Love, Harry Beckwith explains that relatively few businesses actually sell products, services, or even expertise; most sell satisfaction. “Progressive does not sell car insurance. It sells comfort: the comfort of knowing that if you have an accident, they will be at the scene, ready to write a check.” In the same way, great salespeople don’t try to sell items or programs. Instead, they appeal to and connect with their clients through emotion, brand story-telling, and thought-leadership. In doing so they take the attention off price and features and appeal to the feelings customers value and the identities they want to experience and express.
  • Great brands ignore trends. Great salespeople don’t imitate, they innovate. Great brands don’t follow what everyone else is doing, nor do they wait to take their lead from customers. In the same way, great salespeople offer their customers unique perspectives and often seek to push their thinking. They present a differentiated sales experience by challenging customers’ status quo and teaching them something new and valuable. They are the “Challengers” that Matthew Dixon and Brent Adamson identified in their research into what distinguishes high sales performers.
  • Great brands don’t chase customers. Great salespeople attract the best customers for their company. Just as great brands know they’re not for everybody and so they seek to attract loyal and profitable customers through shared values and common interests, great salespeople are selective when engaging prospects. Research by VoloMetrix, a sales productivity firm, shows that top sellers build deeper relationships with fewer customers rather than casting a wider net of shallower engagement. Salespeople cultivate profitable, sustainable customer relationships if they’re savvy enough to focus on accounts that inherently represent a good fit with their company instead of trying to close as many deals as possible.
  • Great brands sweat the small stuff. Great salespeople create extraordinary experiences that embody their brand. Great salespeople know that they can strengthen their brand if they interpret and reinforce it and its differentiating value throughout the sales experience. So they examine all the different touchpoints between the customer and the brand in the sales process and seek out opportunities to infuse the most influential ones with the brand’s key values and attributes. They’re also aware of the power of social selling today and they carefully manage their social network activity to make informed, authentic, personal connections.
  • Great brands never have to “give back.” Great salespeople create real value for their customers. Great brands don’t engage in questionable business practices and then try to make up for them with charitable activities and social responsibility programs — they create a positive social impact in the way they design and run their businesses. Likewise, great salespeople don’t engage with customers simply to make a sale — they look for ways to make their clients more successful. Leadership consultant Scott Edinger observed, “Sales-training programs rightly focus on finding clients’ ‘pain points.’ But great salespeople also know there’s value in pointing out successes waiting to be exploited.” They know improving a customer’s condition may not always involve a sale and they do it nonetheless.
  • Great brands commit and stay committed. Great salespeople impart the unique value of their brand. Many salespeople feel pressure to gain new business or retain accounts at any cost, but the most effective ones do not give price concessions just to win deals. They are convinced of the value their company offers and they skillfully help their customers understand it as well. They employ the techniques put forth by the writers of the book Value Merchants, drawing on their knowledge of what clients value to convey their offer in a way that resonates with them.

Great salespeople implement all of these principles in a cohesive, coordinated approach that mirrors the brand-as-business management approach used by great brands to develop powerful and valuable brands. Just as great brands cultivate mutually beneficial relationships with their customers, great salespeople cultivate a deep connection between their company and their client’s business. To borrow a term, the best salespeople are brand evangelists.

Guy Kawasaki first adopted the term “evangelism” into the business world by applying it to an innovative approach to sales, marketing, and management. Evangelism, as he defined it, means “convincing people to believe in your product or ideas as much as you do” because evangelists believe that what they offer is truly helpful and valuable to others.

Over the years, many technology companies have developed the role of a technology evangelist or “chief evangelist.” These people are charged with building up support for a given technology, and then establishing it as a standard in the given industry. Like these technology evangelists, brand evangelists — that is, great salespeople — build up support within a market for a brand so that it becomes the brand leader in its category.

Importantly, brand evangelism is not another one of the customer-centric or customer-driven sales approaches that have become popular in recent years. Customer-centric sales and most other sales improvement approaches are pursued for the sole purpose of increasing sales. Brand evangelism is about engaging customers in a way that produces stronger and more valuable brands and sustaining long-term business success for their companies and their clients.

 

This is what great salespeople do.

 

Two Yardsticks for Measuring Risky Decisions

How Women Decide: What’s True, What’s Not, and What Strategies Spark the Best Choices by Therese Huston is a fascinating book. How do you make decisions? Do you know the risk in making your decision? Below is an excerpt from the book:

Two Yardsticks for Measuring Risky DecisionsHow women decide.jpg

Are there strategies for figuring out when to take a risk? I was torn on whether to include this advice because I don’t want to send the message that women are, underneath it all, fearful of risk. The data doesn’t support that. But whether you’re a man or a woman, someone who takes too many risks or too few, you need strategies for evaluating new opportunities. There are any number of risky decisions you might be considering. Maybe you’re thinking about taking a new job or quitting your current one. Maybe you’re trying to decide whether to invest your time in a project that your friends think is a dead end but that you believe is just beginning. I’m going to offer two tools, two yardsticks you can use to measure a daring move and whether it’s headed in the right direction.

The first tool is the 10-10-10 rule, developed by the journalist and author Suzy Welch. The purpose of this strategy is to help you look at a decision from three angles, with the hope that one of those vantage points will provide a pop of clarity. In her book 10-10-10, Welch offers three easy-to-remember questions: “What are the consequences of this decision in 10 minutes? In 10 months? In 10 years?” Simple, yes, but potentially quite powerful. The goal isn’t to constrain you to those exact numbers – you could think about two days, six months, and seven years from now. The goal is for you to think about the immediate consequences, the impact your decision will have in the foreseeable and imaginable future and in a distant part of your life, a time far enough in the future that you can’t predict the intervening details or events but you still have clear hopes for yourself. Imagining forty years out is probably too far. The idea is that all too often when we’re trying to make a decision, we’re focused on one, maybe two of these time frames, but wisdom might lie in considering all three.

The second tool for sizing up a risk is something called a premortem, a strategy discussed in the bestseller Thinking, Fast and Slow, by Daniel Kahneman, a Princeton University professor and Nobel Prize- winning economist who has been studying reasoning and decision- making for over forty-five years. You may be familiar with a postmortem, which is what you do when a project or event is over, but a premortem is just what its name suggests – a step you take before the project launches, before you’ve committed to a plan of action and the risks that come with it. The concept is simple. Once you have a concrete plan on the table, bring together the key people who know about the decision you’re making and say, “Imagine that it’s a year into the future and we’ve gone ahead with our current plan. The result was a disaster. Take five to ten minutes and write down a brief play-by-play of that disaster

You might not be immediately impressed with this strategy. You’re thinking, But I’ve already asked “What could go wrong?” a dozen times. But that question involves looking forward, to possible events in the future, whereas the premortem involves looking back. (A premortem is similar to the look-back we discussed in chapter 1.) Looking back may not seem like much of a shift, especially since it’s all in your imagination, but this small shift in perspective can be profound.

Consider these two questions: “How likely is it that an Asian American will be elected president of the United States in 2024? Why might this happen? List all the reasons that come to mind:’

Before you read on, take a moment to think about this future possibility and generate some ideas.

That was looking forward. Now consider these two questions: “It’s 2024 and an Asian American has just been elected president of the United States. Why did this happen? What events might have preceded this one? List everything that comes to mind.”

If you’re like most people who’ve been asked these questions, a wider variety of vivid details come to mind in the second, hindsight scenario. It’s not just that you’re getting a second chance to think about the same event – people generate better answers to the hindsight questions even if they never heard the first ones. Deborah Mitchell at the University of Pennsylvania, J. Edward Russo at Cornell University, and Nancy Pennington at the University of Colorado collaborated on a project and found that people who are given the second, hindsight scenario generate 25 percent more reasons than people given the first, foresight scenario.” Perhaps even more important, people generated more specific and concrete reasons in the hindsight scenario. When we think about future events, we’re content to think in broad generalities, but when we think about something that has already happened, we feel a need to provide more convincing explanations. This is why the premortem is so effective- it’s looking back at a fictional event as though it’s happened. You’ve always heard that hindsight is better than foresight, and that, remarkably, includes imaginary hindsight.