One of the most important things I learned as an entrepreneur is that, surprisingly, a large part of my job was to be a salesperson. And selling – whether you are fundraising, pitching, or actually trying to find buyers for your product – is really about language. There is a great deal of meaning in the words we use, the way our words are phrased, and the various verbal constructs (intonation, cadence, tone, etc.) surrounding the message. The importance of language in the sales process is often sorely underestimated, leading to a general misunderstanding of your pitch, their needs, and ultimately – why they actually said “no”.

Remember this – Getting to the “close” is about paying attention to “prose”. (I’m sorry…that was horrible…I just couldn’t help myself)

Before we dive into tactics, a quick primer – one of the product leads for Airbnb once told me that an internal mantra for their engineering team was “the whole screen matters”, meaning that team members needed to prioritize every single item that appeared on a user’s screen, since they were all equally important. In your sales process, the same is true – the whole screen matters, except think of each communication as part of that screen. Newbies often make the mistake of over-emphasizing the pitch itself and ignoring all the communications that happen before, during, and after the pitch. The point is – you need to be vigilant and care about the language used by all parties in every single email, call, and meeting so you can build a strong case for the “sale” & gain insight into what they really need, want, and think.

Below we’ll cover 2 main areas – 1) Vocabulary, and 2) Writing Composition (pitch, email, proposal, etc.). It all sounds like 6th grade again but remember – there is a specific language for closing deals. Think of it as another kind of ‘code’…


Simply put, every word that comes out of someone’s mouth matters. Your words and the way you say them are very powerful and sometimes convey a deeper meaning, whether intentional or not. But when you become really adept at sales, you realize that your true power is listening, not talking. The reason for this is because when you really listen to someone, you can focus in on 2 “decoders” of the sales process – 1) the words they are choosing to use, and 2) the way they are saying those words. For those unfamiliar or unsuccessful with sales, this is an area that is greatly misunderstood. They tend to think that selling is just about “what you say & do” to be persuasive, and they tend to take the targets’ words at face value. Let me unpack this a bit:

  1. The words THEY are choosing to use: Persuasion is more about listening, less about talking. Newbies often start out by talking, and often they won’t shut up. Then once they discover how ineffective this is, they often begin talking less & hearing, but not listening. Here’s the problem – your job is to gather as much information about your target before you can sell anything. And the best way to learn is to listen. However – people often talk in “code”. By this, I mean that most people aren’t very direct or forthcoming, so they won’t tell you exactly what you’re trying to learn. This is perhaps a function of general discomfort with the sales process (on both ends), or of the polite culture we live in. The bottom line is that there is a distinct difference between hearing & listening. Hearing is taking their words at face value. Listening is understanding the meaning behind the choice of those words, and drawing insight. With time, you will begin to notice verbal patterns here. I found that my targets had a pretty common “language” they would use to signify things like budgets, decisions, authority, urgency, appetite, roadmaps, and other key elements of the equation. This was, by far, the most difficult area for me to learn so you need to be patient in the beginning.
    • Note – The words YOU are choosing to use & how you say them: Listening is more important than talking, but make no mistake – your words matter a lot. You need to pay special care to what you are saying and how you are saying it. My best advice is to a/b test language, just like you do with product. Try different words, phrasings, and vocal cues, and begin measuring the reaction. You’ll start to notice a cultural “norm” that is specific to your industry and/or region, and this will open a whole new world…where you realize that words in conversations are like steering wheels in a car.
  2. The way they are saying those words: The other part of listening in the sales process is picking up & understanding tone. There are many ways to say something: quickly, with a sigh, excitedly, anxiously, softly…tone is a reflection of emotion, and will be a critical tool in “decoding” what someone is actually saying. It’s also something you can pick up when you listen vs. hear. Pay attention to the cadence, intensity, & inflection of their words. I found that the “white space” – areas where they hesitated – were particularly revealing because that was clearly an area that was important to phrase correctly (and thus a key problem or opportunity). Sometimes it’s more about what they don’t say vs. what they do say. I’ll expand on this later, but the big takeaway is that you need to not only listen to words, but you also need to listen to the way the words are said, as well as the “silences”. Selling isn’t “talking”. And it’s not “hearing”. Selling is listening.

Here are some tactical vocabulary & phrasing tips I learned (and tested continuously), which worked well for me…


crash landing

  • Avoid Self-Minimizing – Though it’s a colloquial tendency, I try not to start sentences w/ “I just wanted to…” because it is self-minimizing, as if your message isn’t very important. Instead, be more direct like – “Since X is happening, I’m calling about Y”.
  • Set a Casual Tone – In Silicon Valley, the vibe is pretty casual which is an advantage for you, because setting a relaxed tone is like a ‘Fast Pass’ to building a connection with someone. I use pretty informal language and tone, as if I am talking to an acquaintance. For example, I usually start phone calls with “Hey [Bob], how’s it going?” instead of “Hi [Bob], how are you?” – it may seem like an inconsequential detail, but it helps to create a relaxed tone from the start and created a noticeable difference in energy level. To be clear, “casual” does not mean “unprofessional” – rather, it’s just a relaxed, straight-forward way of talking that allows everyone to feel at ease, which then leads to more open discussions. As another example – in email, I use “Hey” as a salutation instead of “Hi” or “Hello”, although this is just the case with men. Weirdly, I found that women were more responsive to “Hi” unless I knew them well – I’m not sure why, but response rates were noticeably higher every time I tested this. I wouldn’t get too cute with salutations, the point here is that my close rate was higher when the vibe was casual and when I tested variables (even the ones that seem inconsequential) and optimized accordingly.
  • Channel Bobby Fisher – If I’m calling someone off the cuff, I never (ever) ask people if they have a few minutes to talk. The reason – everyone is busy and they will almost always ask to call you back, and then (often) forget – which puts you in the position of having to chase them down again…not exactly an attractive stance. It’s important you walk through the chess moves so you can figure out your next best move. Also, even though it’s undoubtedly polite to ask if you are calling at a good time, it’s also (subconsciously) subordinating. You are worth the call (otherwise you shouldn’t be calling), so it’s better to assume they can talk vs. inciting the belief that perhaps your call isn’t very important at the moment. Instead, I say “I wanted to chat with you about X”. Most times they will stop what they are doing to discuss. Even if they need to call me back, I at least decreased the odds of a missed communication and maintained a respect equilibrium.
  • Stop Apologizing – “I’m sorry” is an extremely over-used phrase in our culture, and I reserve it only for times when it’s really needed (i.e. when screw-ups happen because of something I did). Many of the folks I mentored had a tendency to say “I’m sorry” at the drop of a hat without realizing the energy that phrase was bringing to the conversation. It would essentially lower their power dynamic in the situation, and (again subconsciously) decrease trust and/or respect. This doesn’t mean you don’t care about the other person or you don’t acknowledge missteps – it simply means you avoid apologies and find another phrase to address the situation, unless there is something you did that really screwed something up. And even then, the “I’m sorry” is much less important than the fix…so focus on the fix, not the regret.
  • Ask More Questions – I also never ask someone “Is this something you’d be interested in?”, either on the phone or in email. It just sounds desperate, and also is an indication that you don’t know what they are interested in…which means you should be asking more questions vs. pitching. Likewise, I don’t ask people “What can I do to help you”? It’s a lazy question that means you aren’t asking enough questions. You should learn so much about a person that you know whether you can help them or not, and how.
  • Mimicry is Natural – I adjust my words, tone, and cadence to reflect the person I’m speaking with, which is actually something we do naturally in person (subconsciously) with our bodily stance. It communicates likeness, which in turn establishes commonality – an important part of gaining someone’s trust. I found that when I spoke with the same energy, tone, and cadence as the other person, they responded a lot better and were generally much more open to my message.
  • In the Beginning, Avoid Discussing Numbers & Minutia – I generally avoid talking about prices and minute details in the early phases of discussions – it’s interesting because I would always be asked this question, however I had a higher close rate when I kept the conversation more about their needs and my story & “product”, as opposed to pricing and fine print details. So – what they are asking you to answer is not always what they will be most responsive towards (see the “Sand Trap Questions” below). When asked, I would make like a politician and usually sidestep the question by saying something like “We try to keep things simple so we have 3 levels, I’ll send you all the details so you can take your time to figure out which works best for you”.
  • Don’t Be A Bad Date – While transparency is a good thing, the question really is “how transparent?”. Think of these interactions like dating. It’s great to keep it real…but would you go on a 2nd date with someone who spent 15 minutes on the first date telling you all the times they screwed up past relationships? If you are asked about a time you failed or came up short, answer the question with vigor by focusing on the very interesting things you learned, and how you optimized the product or process, then move on.
  • Use Positive Bookends – Because I focus on the positive, I try to deliver news from that filter – even if it’s a tense or negative situation, I always frame & conclude sentences with a “yes” perspective. This is genuine – almost every crappy situation has an underlying opportunity, and your job as an entrepreneur is to be a connector of opportunities…so it’s important you not only have that vantage point, but also that you lead others toward it. Be careful you don’t package sentences with “unfortunately” or other negative words. Find the “yes” and the upside in everything and deliver your words from that filter. Be honest, but be positive also – and make sure you “bookend” the words in your sentences with positivity – it will help steer the conversation in that direction.
    dumb & dumber
  • Anatomy of a Conversation – I like to keep conversations fun & light-hearted at the “bookends”, and meaty in the middle. That way, we break the ice at the beginning, truly learn about each other in the middle, and then conclude in a way that leaves them on a good note. There are several devices that can lighten the mood which I’ve found to be helpful for both parties, like telling funny anecdotes, sharing relatable details, and even a quick laugh at various (appropriate) points in the conversation. My mentor used to laugh a lot, but in a way that was friendly and inviting. If you laugh too much or at inappropriate times, it obviously backfires because, well, its weird. But don’t underestimate the power of these various verbal devices…they essentially convey to the other person that you are listening and are interested in what they have to say, which adds to the relaxed tone.
  • You Don’t Need to “Touch Base” & “Close the Loop” – Remember that you are talking to a human, so you need to make the conversation real. All too often, people talk in “business language” which (to me) sounds fake, cold, and calculated. When you speak authentically, your voice comes from the diaphragm which gives it a more direct, resolute sound. Your tone flows more naturally, as if you are speaking in stream of consciousness. You pause in natural places, you laugh here and there, and you use intonation, cadence, and emphasis. That said, while you want to keep it real, you need to be careful not to confuse this with getting too casual or too personal…this is still a business call, so dropping f-bombs or talking about your hot date tonight is probably not going to win you any deals. Instead, focus on speaking authentically, casually, and resolutely.
  • Steering vs. Riding Along – It’s important to pay attention to who is controlling the conversation. Otherwise known as power dynamics, there is often a tendency for 1 person to be the “alpha” in the interaction. The alpha takes control, sets the pace, changes direction, and generally dictates the conversation. An ideal situation is where the power dynamic is equal – you both share the reins. This is ideal because you don’t want someone else to monopolize the reins – otherwise they will most likely lose respect for you, subconsciously. Humans are funny creatures – a lot of how we actually feel is generated in the subconscious mind, and one of the things your target will want is for you to be a leader, to guide them, to help them. Thus – if they have the reins and you are just along for the ride, they won’t see you as someone who will lead them to a solution. On the other hand, if you monopolize the reins, you risk making them feel powerless. This depends on their level of ego, but unless someone if extremely passive, I make a point to share the reins equally. You may have never considered who controls the conversation before, but it’s a critically important part of persuasive communication.
    homer fight
  • Get Them to Sell Themselves – I don’t sell anything – I find people who sell themselves on my solution. I often hear entrepreneurs say that it’s always better to have someone else vouch for their product vs. them selling it. However, what if you could get your target user/customer to vouch for it? This is another reason you want to spend more time asking questions, and less time talking. I often ask the other person why they are interested in my solution, what they liked about it, and how they could envision it helping them reach their goals. The objective is to get data from them so you can learn, and also to have them cement their belief that the product is killer (not you), which will create a stronger desire for it. But it’s important to note that a good part of the work is finding the customers who fit your product, not convincing those who will not actually benefit. The latter is the “evil sales” that people often think of, the former is what selling actually is in it’s successful form.
  • Selling to Men vs. Women – Something I’m guessing may be controversial, but it’s something I tested over the years vigorously – As a woman, my voice tends to be rather high-pitched. I found that when I lowered the pitch, my close rate improved. I can’t explain this and maybe it points to unconscious bias, or maybe we humans just interpret lower voices as more serious…I don’t know. I found it interesting that my dog also responds better to commands when I lower my voice, and the same is true of horses. If you’ve ever heard jockeys (men & women) command a horse, they give very blunt, low-pitched cues. So perhaps it’s just a function of…being an animal. Whatever the case, the lower-pitch consistently had higher close rates. I also found that limiting my inflection (the rise in pitch at the end of a word) also led to a higher close rate. I figured it’s because raising the inflection sounds less confident or authoritative. Try this — say “absolutely” with a high pitch on the “y”. Now say it with one, consistent low pitch. See the difference? Again, some folks may be offended by this…regardless, it’s just my experience as to what led to a higher close rate.
    • Indirect vs. Direct – Likewise if I was following up on a proposal or communication, I found a higher response & close rate among men when I said “I haven’t heard back from you”, while women responded & closed more when I said “I haven’t heard back”. If I had to guess, I’d say that “from you” is extremely direct, and for whatever reason it had a higher impact on men than women.


  • Detecting Undercurrents – As mentioned above, I pay close attention to their tone, cadence, & areas of silence or hesitation…all of these combined will give you the “undercurrent” of the message. The undercurrent is often much more telling than the words themselves, because people aren’t always forthcoming, whether or not they want to be. I can’t tell you the number of times one of the junior folks on my team heard someone say “It’s going really well” and believed just that, while I picked up something entirely different. When tone lacks energy, cadence slows, and silence occurs at certain intervals or areas, this will often indicate the more accurate message.
    sheldon cooper
  • Avoiding “Quick Sand” Questions – People are generally used to grinning & bearing though boring, painful, and conventional pitches. As a result, they develop boring, painful, and conventional questions to ask YOU. This, however, is often a (very) unintentional trap…because you will then become at the mercy of their scripted questions, you lose the power dynamics, and you also just lost the ability to make your pitch a unique, interesting, fun conversation. The worst part is that it’s like stepping in dog shit…you make one accidental move and then you just can’t get rid of the stench. In other words, their one seemingly innocent question will lead to another, then another…and you are in quick sand. You will begin to notice the “quick sand” questions with time. I found that when people would ask something like “what is your process for X” or “what have other companies like us found to be successful?” or “tell me about your packages and the costs”, these were the best types of questions to take the reins on & steer a different way. To do so, I often quickly turned the car by saying something like “We don’t really do things that way – we found it better to do Y”, and then I’d begin sharing details about Y and – most importantly – asking them more questions. This was 100% genuine – we really didn’t do “X” and I really didn’t like to run a business in the “box” they were accustomed to seeing…so steering the car in a different direction was not only authentic to my company, it was also refreshing for them & helped the sale close. This advice may feel a bit gelatinous right now, but the specifics are dependent on your product and industry. So just remember to create your own “pitch” and your own story, and be mindful about the questions people will ask you (which do tend to be very similar across targets) which are actually “sand traps”.
  • Avoid Browsers – There are a lot of words which indicate they aren’t buying right now, but just browsing. You need to be very careful about browsers because they are a time suck, especially the ones at large companies that have all the time in the world. Newbies often spend more time trying to convert browsers to buyers, and less time actually looking for buyers. You should probably spend about 80-90% of your time on the latter, and just 10-20% on the former. Some of the words/phrases people would use in my experience that tended to indicate this were “learning”, “exploring”, “getting our feet wet”, and “getting more information”. Interestingly, these were most often the folks who wanted in-person meetings where they brought their whole teams…but never actually were serious about buying. Also, spending too much time with anyone is giving too much, too early – in the words of the philosopher Beyonce – “If you like it then you better put a ring on it”. The same is true in business.
    window shopping
  • Learn the Code Words – There were likewise words/phrases which indicated lack of budget like “we don’t pay to play”, “we prefer to partner”, “we bring a lot of value to the table”…all which were their selling points for an “in kind” relationship vs. an actual sale. Sometimes this is a win…but other times it will just be a time suck. So pay attention to the patterns and you’ll begin catching these “red flags” right away.

I love working with customers. Sales has really influenced everything I do. It has instilled in me the important traits of operating with a sense of urgency and listening to people.
– Jeffrey Immelt, CEO, General Electric


snoopy writing
Before we get into the nitty gritty tactics of writing composition, I need to emphasize the importance of persuasive writing skills in closing deals. In my opinion, the live conversations you have are more about selling your vision, your story, and your product’s basic advantage, as well as finding a connection. But that’s only part of the process – you need to also sell the specific details of the product & “package”, which tends to happen when the target customer sits down to review the “proposal”, share it with their team, and make a decision. Even when you pitch a VC, they often will circulate your deck & other materials to key members in the decision-making process who weren’t in the pitch meeting. Additionally, the communications that occur before & after the “pitch” set the stage & close the deal, and these are many times in writing. So the point is – your writing matters because it’s most often a huge part of the close, and it will most often be read by decision makers whom you won’t even meet.

There are 2 things to keep in mind here:

  • 1 – Persuasive writing is a skill that can be critical to your success since you will constantly need to send pitch decks, proposals, emails, and other communications to arrive at the “Yes, I want that” answer. I’d suggest having a template ready, and then simply customizing the template and sending it immediately after your pitch meeting/call. Otherwise it creates a domino effect of delays, which could end up being the difference between winning & losing the deal.
  • 2 – Email is an art – While there have been many books & conversations about the “death” of email or its ineffectiveness, I have found the complete opposite to be true. I love email. No – let me rephrase that. I LOVE email. The way you structure words, sentences, and phrases, the tools you use to call attention to various portions, the length, the choice of words, the subject lines…all of it creates a feeling for the recipient (hence, the art). You need to take into consideration the attention spans you’re working with (hint: most people today have the attention span of a flea), the call to action you are inciting (just like your product funnel), the urgency you’re creating, the implications of the words you’re using, and the various devices you can use (bolding, highlighting, underlining) to achieve the effect. In the end, all of these elements create a feeling. Email is an art form, and it can be a powerful tool in your sales process, whether you are selling a product, fundraising, trying to land a huge distribution partner, or just trying to score a meeting.

Here are some tactical persuasive writing & email tips I learned (and tested constantly), which worked well for me…


  • Visual Road Signs – Most people don’t read very carefully so you need to use visual elements so the information is eye-catching, digestible, and retained. Your writing should be condensed (only the necessary words included, all other “fat” cut out) and must be easy to read (think: bite-sized). Since people don’t read thoroughly, you need to give their brains “road signs” which will not only maintain their attention, but will also generate stronger retention since you essentially did the navigation work for them. These road signs include the devices below. Note that there isn’t a hard & fast rule here, which is why I use the word “art” to describe the visual component to composition…it’s all about how the email or proposal makes you feel after reading it.
    • Bolding – I use this mostly for headings & key words/phrases that I want the reader to notice (especially impressive numbers/stats/figures and well-known names of people or companies (customers, users, etc.) that help “sell” the pitch)
    • Bullet Points – I think the bullet point is critical — when it makes sense to break a paragraph into 5-7 bullets instead, do it. I use bullets constantly because they are easier to read, more digestible, and they also provide more emphasis to each point. In more complex communications, bullet points with a bolded “heading” in the beginning help the reader to quickly make sense of the groupings.
    • All Caps – With the exception of subject lines (see below), I don’t use all caps much. It feels like yelling…and honestly reminds me of Will Farrell’s voice immodulation character on SNL.
    • Parenthesis – When sentences begin to feel too word-packed yet paring down further will detract from the message, I often use parenthesis because they visually break up the word overload and make it more bite-sized.
    • Highlighting – This is a very under-utilized visual device and it’s immensely helpful because the reader’s eyes WILL naturally dart to highlighted words/phrases. I often highlight the CTA and/or the deadline. In the past, I have also used different colors of highlighting but only in situations where I wasn’t trying to close a deal since it can be a rather forceful device. But with the right people at the right time, it’s magic.
    • Underlining – I much prefer underlining to italics (see my hatred of italics below) though I use this sparingly as too many underlined words can create visual chaos.
    • Colored Text – We all know this is Dave McClure’s specialty, and I often take a cue from him since it, again, makes certain words POP. I tend to use a red or blue, which stand out most. That said, I rarely use more than 1 non-black font because I think it creates visual chaos for my purposes. Instead, I rely on bullets, bolding, and highlighting for extra emphasis.
    • Italics – I despise italics (yes, I used them several times in this post but only because my WordPress theme is limiting). In proposals & emails, I find italics to be a lazy visual device that don’t create a lot of visual impact. I prefer bolding instead.
  • Structure
    • Subject Lines – Consider the emails you open…what makes you do so? You want to be careful here not to be schlocky, since nobody likes spam. I have found the highest open & response rates involve straight-forward subject lines that tell the reader exactly what I’m writing about but also are eye-catching. I tend to use a 1-2 word “customized hook” at the beginning, then a visual element (>, : . – , etc. ) that directs the reader’s eyes towards the content of the email (example: Mary > 500 Startups / 2014 Partnership). Note that my hook is often their name or company name, or sometimes even their company name followed by mine (Acme / 500 Startups > Info + Next Steps). On some occasions, I use ALL CAPS for the hook…but only when it’s a critical email and/or I’m trying to get large groups of people to do something (i.e. not a 1:1 situation).
    • The 1st “Paragraph” – I use a 2-3 sentence max intro in each email which details why I’m writing. It’s a quick “road sign” to tell the reader where they’re heading. As an example – “Hey Bob – Hope all is going well. Per our chat today, below are more details about about the 2014 Acme / 500 Startups partnership…”). As you can see, I don’t spend too much time at the beginning on niceties (i.e. “it was great learning about you & how awesome that we have the same kind of dog, and how great that our kids go to the same school, blah blah blah”) because time is SO limited and inboxes are SO chaotic…so I get to the point.
    • The Meat – As mentioned above, I use bullet points and other visual elements to ensure the “body” of the deck, proposal, and email aid the sale. I keep emails brief (no more than 3 punchy paragraphs usually), while I make decks and proposals pretty detailed yet visually digestible. My sentences are always condensed though – only say what you need to say, not a lot of extra fluff. A good writer understand the powerful words and elements, and relies on that…not endless blabber.
    • Call to Action (CTA) – Just like any funnel, every email should have a CTA (what you want them to do & the deadline) that is obvious to your reader. I use bolding, underlining, and/or highlighting to indicate the CTA in my emails. When you have a long email (which I would generally discourage but sometimes can’t be avoided), its better to put your CTA at the top & the bottom too (just as you do on your website) since its easy for the reader to forget, given the mass of info. Here’s an example of a previous CTA I used when I was closing a deal (remember – the deal isn’t done until a contract is signed):
      Screen Shot 2014-10-28 at 10.47.21 AM
    • Interesting Data – End with a Question – I found a consistently higher close rate when I closed (certain) emails with a question, rather than a statement. In the old days I would say something like “Let me know if we’re confirmed”. But when I tested that against “Are we confirmed?”, the latter almost always won. There are times when I wanted to create a cooler vibe, and I ended with a straight-up CTA (like in the CTA screen shot above) that included a deadline, instead of a question. But when I was trying to get the person towards a decision or get a quick answer (i.e. when the situation didn’t require a more gentle approach), a “question towards action” at the end was extremely effective.
      ron burgandy
  • Grammar – Direct Sentences vs. Run-Ons – I found a higher close rate with a very direct, straight-forward tone. I try to avoid run-on sentences which is interesting because I’ve noticed that young folks use a TON of run-ons…did they stop teaching this in school? Regardless, attention spans are short so you need to get to the point quickly…so cut out the fat, and use visual elements (above) to make your content more digestible.
  • Know Your Audience – The “Who Cares?” Filter – All good writers understand their audience, and you should be no exception. Who are they? What do they actually care about? What did they emphasize over the course of your communications? Make this the framing of the entire proposal, even if it means more work for you.
  • Photos & Visuals – These are critical elements in my formal proposals because a photo conveys so much and also creates a good visual cadence (text to image ratio) for the reader. I don’t worry if it makes the file heavy…I’ve never had anyone complain about file sizes, and visuals make the proposals that much more enjoyable to read. That said, I mostly use photos that are personal to my company (not random photos scraped from Google Images) and I don’t go overboard since I’m really looking for balance and emphasis. This isn’t a proposal from Ansel Adams, so be careful not to include too many visuals or the proposal/deck will feel like fluff.
  • Personalization & The Field of Dreams – Personalization is an important device, because it allows you to paint a picture of your solution/product in their hands, which when repeated is a planted seed (in their minds) of your “future together”. My proposals almost always include personalization, and I often find it helpful (even for myself) because it better enables me to consider the audience as I’m writing. So for example – instead of using a headline like “Proposal” you can say  “Acme Corp + 500 Startups – Partnership Overview”…and keep reiterating the cooperation throughout.
    field of dreams
  • Deadlines – For quick responses and communications, I set deadlines that are no more than 2-3 days out because the world moves quickly, and 3 days for a busy inbox is pretty much an eternity. But for larger deals & decisions, your deadlines should really depend on the situation…what is the standard amount of time for a decision given the deal type, industry, etc.? I tend to push limits a bit here because as a startup, your time is likely way more expensive than theirs. But as an example, while I typically don’t let a deal drag out longer than a month, I once had a deal that took 11 months to close because it was a large financial institution (i.e. they couldn’t move quickly) and it was a large enough deal to warrant the waiting game. That said, I didn’t put much time into it after a month (remember: only spend 10-20% on “browsers”), and just did quick email check-ins every month until it closed.
  • Follow-Up – For a 1st or 2nd follow-up, I have found that email works great but the trick is to make them very brief. I usually say something like “I haven’t heard back from you re the below proposal — any update?” (i.e. end with a question). And as noted above, avoid saying “just” as in “I just wanted to follow-up”, since it’s self-minimizing. If I follow up twice via email and don’t hear back, I pick up the phone (no need to schedule a meeting for this) and say “Hey Bob, I haven’t heard back yet so wanted to check in — any updates on your end?”.
  • Things to AVOID Doing
    • Don’t pitch anything over email – it’s never a substitute for calls or meetings, and it rarely is successful. It’s also a sign of weakness – you should be able to say anything of substance to someone in person or over the phone, and use email to augment the process. However email is NOT the process.
    • Don’t quote prices over email – You should absolutely add this info to your deck or proposal, but think of email as part of the romance. Nothing will kill that romance more than getting to the point too quickly…your emails should “court” the other person and incite trust. While we all know this is about business, there’s something that is still tacky about putting a price tag on everything…it cheapens the relationship if it’s not done carefully. So use email to relay information, cement interest, and incite action.
    • Don’t use too many exclamation marks and smiley faces!!!! 🙂 🙂 🙂 – This is really a personal preference, but like Elaine on Seinfeld, I think the exclamation point is not how we really ever speak. And don’t get me started on the smiley face – while I admit that I use it sometimes, I think overuse of both devices is often an indication that the writer is uncomfortable with being straight-forward, which (subconsciously) can incite a lack of respect from the recipient. It’s the equivalent of saying “I hope it’s ok that I’m saying this”, sort of like passive aggressive punctuation. In itself, it’s innocuous…but when you are trying to close an important deal, just be straight forward and say what you mean.
    • Don’t lie – Ever. Never. It will always come back to haunt you. Remember – selling isn’t about closing the deal, it’s about making connections. By making yourself invaluable to a valuable network, you will eventually win more games than you lose. So play the game with honesty & respect.
    • Don’t exaggerate – In law school we had something called the “straight-faced rule” – you could only make an argument if you could say it with a straight face. This is a corollary to “Don’t lie” above – exaggeration is the younger cousin of a lie, and anyone adept in business will smell the B.S. from a mile away. It’s unbecoming, it’s a sign of someone who ought not to be trusted, and it will damage your reputation. So again – be honest & straight-forward with everyone you meet.
    • Don’t forget to have fun – We spend so much time at “work” that, at the end of the day, our co-workers, investors, partners, and associates become a huge part of our lives. Wouldn’t it be a shame to go through so much of your life without enjoying it? Many people think this needs to be relegated to weekends and holidays, but I absolutely disagree. The relationships I’ve built while starting & building companies are really special and frankly – really fun. I love learning about people, helping them through various challenges, and accomplishing great things together. So in the midst of all these tips about how to close deals, remember to relax & enjoy yourself. This is the time of your life.

Success is the ability to go from failure to failure without losing your enthusiasm.
– Winston Churchill

Christen O’Brien is a co-founder & Managing Partner at
500 Startups, an early-stage venture capital firm based in Silicon Valley with 800+ portfolio companies around the world. She built the Business Development group which has created much of 500’s corporate, community, marketing, and educational initiatives on a global scale. Previously, Christen founded a content company, led fundraising, sales, marketing, and business development across multiple industries, and also served as a volunteer in the Peace Corps. She lives in San Francisco with her husband Paul and their Great Dane, Virginia Woof. You can contact her via email (christenmarieob at gmail) or via LinkedIn or About.Me.











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