Risk isn’t necessarily Harm

The term “risk” gets batted around projects like a ping pong ball zipping around a startup. It’s everywhere. Your schedule is at risk. Your budget is at risk. Your resources – fraught with risk. Your scope is basically nothing but risk.

But how often do we really stop to evaluate what we’re (a) worried about and (b) able to manage?

Fundamentally, each dimension of a project is of course going to have risk, in the sense that something incomplete could not get completed. It might not be completed by a certain time (schedule risk) or at a certain amount of money (budget risk). But are we sure we’re properly equating risk with harm?

Harm is bad. We want to avoid harm. The notion of harm insists that there’s a consequence to a bad outcome. Risk… Is a little murkier. It implies that there are consequences, but the nature or impact of those consequences may not necessarily hurt.

Here’s an example: Your sponsor walks in the door and says, “This new software application is critical for our 3rd Quarter sales numbers. So you must have the project complete by end of June.” Now you’ve established a time-box, and all future decisions (scope, budget, resources, etc.) are likely derived from this boundary. Slipping any of those facets might result in increasing the risk of your project. But can you clearly articulate the harm? This is where an honest discussion needs to happen with your sponsors & stakeholders.

The Discussion:

Product & Project Manager: You said that the app is CRITICAL to 3RD QUARTER… Can you define those two things?

Sponsor: Not really. I’d just really like to have it done by September so we can train everyone during the holiday slowdown.

Sometimes, it’s that silly. The 3rd quarter really means the 4th quarter, and critical really means “nice to have.” But, sometimes the discussion can be direct, and creates a measurable structure to evaluate risk:

Sponsor: Sure – We think that this will boost our sales team performance by 5% per person. Right now my average salesperson is doing $120,000 per month, so I’d like to net an extra $6k per person per month. Across our 10 salesperson team, that’s $60k incremental per month, starting July. That gives us an additional $360k revenue for the year.

Product Manager: Which features in the scope are the ones most directly associated with the revenue bump you’re looking for?

Sponsor: [ Points to 1 “magic feature.” ]

Now you’ve established your risk profile: Every “day” of slippage past June 30 is going to cost the company something like $2,000. Also, you’ve found the #1 item on the deliverable that without implementing nets actual harm to the project. If that feature doesn’t work right, the whole “app” might as well be useless.

These sorts of discussions can be tricky, so have them at the right time (hopefully early – before you’ve committed to anything) and with the right people (ideally, the sponsor / product owner). But now, if a resource slips on a non-essential feature, you can at least differentiate between harm and risk in a meaningful way.

My Favorite Podcasts for Business & Creative Thinking

There’s something overwhelming about digital media these days. Whether it be trying to figure out which of the dozens of new Netflix releases might actually be worthwhile, or having all music from all time available at a tap, or trying to catch up on news & events in your Twitter feed – there’s just a lot out there. It’s too much for anyone to keep up with. I feel the same way with podcasts – there’s an unbelievable amount of great material out there, and frankly I pity the poor person who has enough of a commute to really take advantage of it all.

Some friends and I were together for lunch a few weeks back and struck up our favorites, so I figured I’d share some of mine with the world. Here’s a few of my favorite podcast episodes, which I find really worthwhile as a burst of inspiration and creative thinking during a commute or a trip around town.

Note: All links are to iTunes / Apple Podcasts. 

Freakonomics Radio: When Willpower Isn’t Enough from March 11, 2015 – There’s a topic in here called temptation bundling that has really stuck with me over the years. It’s a really simple idea: pair something you want to do with something you should do. I’ve used it this year to shed more than 20 pounds by pairing Netflix show watching with my elliptical workouts. I now have an almost pavlovian reaction to the idea of watching a “binge-worthy” show that I’ll need to be working out to see it. Great episode, and the Freakonomics podcast is my absolute favorite.

How I Built This: Barbara Corcoran from April 24, 2017 – Guy Raz is a supremely talented interviewer and the production / editing of these podcasts is great. In this particular episode, I found Barbara Corcoran to be a tremendously inspiring person – both that she overcame many technical & professional obstacles to create her business, but also plenty of drama in her personal life. Double-underline hustle. This is a great episode to start on if you’re interested in hearing some worthwhile business founder stories. As an aside – I can also recommend you skip the episode about Rolling Stone Magazine – there’s absolutely no drama in that one. You can tell even Guy is getting exasperated by the lack of conflict or adversity, which for a supremely talented interviewer is no small feat. 

Decrypted (Bloomberg): … Build a Startup Outside Silicon Valley from February 27, 2017 – This series from Bloomberg bounces around many different topics any given week, but this episode certainly feels relevant to someone like me who is “tech” but no longer in the Bay Area. There’s another great stretch of Decrypted episodes from April – May 2017 that seemed to focus on a lot of Chinese & Asia-tech topics, always of interest to me given the time I’ve spent in Macao, Hong Kong, and Singapore. Silicon Valley may have an edge today, but the startups of the future are more mobile than we may realize.

Planet Money: #682 When CEO Pay Exploded from February 6, 2016 – This is another well produced podcast with a consistent format and a worthwhile use of the ‘Subscribe’ button. I think the topic of CEO pay is an interesting one, and this is a good fact-finding episode for that discussion. The only issue with Planet Money is that some of the episodes are more like testing-grounds for other NPR shows, so don’t be surprised if you get something other than economics or business topics. It can often be a good diversion, but if you’re in a mood for steak, no point in someone handing you a piece of kale and saying ‘try it!’

So those are my staple podcasts – Freakonomics Radio, How I Built This, Decrypted, and Planet Money. Here’s a few more that I’m just starting on:

Revisionist History with Malcolm Gladwell – Much like having Steven Dubner host the Freaknomics radio podcast, having Malcom Gladwell host this show really provides an authenticity and perspective that prompts deeper thinking and consideration. I’m only a few episodes in (starting at the beginning) but already I’m enjoying the narratives, and the Gladwell hook is always enjoyable.

Trailblazers with Walter Isaacson – Again, another world-class author has taken to narrating his own podcast, and the results are a thoughtful journey through a bi-weekly topic of disruption. Clear storytelling and a great emphasis on the full history of the topic makes this one a worthwhile listen even for stories you think you already completely understand.

So those are a few of my favorites. I hope if you’re stuck looking for some podcast amusement you’ll give them a shot, because I’d love for their audiences to keep growing so they’ll keep producing them! What I really can’t fathom is how these high-quality productions stay in business? The podcasts themselves typically only include a couple commercial plugs, and even those are done in a low-key and unobtrusive manner. I hope whatever the rewards are, these creators continue to produce great stories and share them on this medium.

Do you have any suggestions for me? Please leave a comment or send me a note on Twitter with your suggestions (Twitter.com/heydavecole). Thanks for reading!



The Servant Leader

One of the core tenants of any good Agile practice has to be the openness and transparency of the exercise. There’s little room for opacity in a well run Scrum – both within the development group as well as with the business team & users. One of the phrases that I both love & hate is the expression: Servant Leader.

I love the concept of the Servant Leader because it immediately conjures images of someone in an authority role serving those who he* is responsible for. It inverts the traditional image of “boss” and “worker.” Thanks to this inversion, you’ve effectively cleared the mental reasons for someone in a worker role to avoid sharing an idea, opinion, or concern. At the heart of Agile is the need for the leader to quickly understand the true facts of the situation, whether it’s an estimate that’s turning out wrong, a requirement that’s incomplete, or a technical hurdle that needs more hands. In a Servant role, it’s my responsibility to take care of the hassles, nonsenses, and nuisances. Cook the food, feed the troops, clear the table, and get ready for the next meal.

Thesaurus entries for the word: Servant… Not particularly uplifting…

I hate the concept of the Servant Leader because it’s not really authentic. Sure, I’m going to do whatever I can to make you happy – but if I’m not sold on the results there’s no real question of how these roles are going to change. You’re going to be responsible for the outcomes and I’m going to be responsible for figuring out if there’s any consequences. This notion of servitude and being subject to each other can compete with traditional structure and focus. The expression “servant” seems dated, and in our modern language might seem insensitive. I don’t have any first-hand experience with this (I’ve never had a coworker or colleague say that it’s offensive) – but if it were, I wouldn’t be surprised.

Continue reading The Servant Leader

Opportunities for Data Innovation are All Around Us

I just recently finished reading Sexy Little Numbers by Dmitri Maex. It’s a very timely and interesting look at some of the data trends that anyone can and should be accessing using the customer data and insights they already have around them. What was striking to me was the presence of statistical modeling in the book – the opportunity to yield useful and actionable information in the presence of data-sets that you probably already have in front of you.

The opportunity to use data creatively to yield useful results was absolutely present during our development of Dashter. And its worth thinking about within your business as well… What data do you have – and how can you use it to your advantage?

Here’s a couple examples from within Dashter where we developed greater value by tapping the data that we were already pouring in to.

Trending in Friends

One of the first things that a Dashter user sees on their homepage is the Trending in Friends pane. Within there, we provide 18 “trends” that are collected from a gathering of ~200 tweets from your timeline. So what does it do? Well, basically, it just adds up all the hashtags found in those ~200 tweets, and then shows you the top 18, in rank order from most-used to least-used (of the top results).

Why is this useful? Well – when exploring Twitter, its often hard to get a grip on all the data swirling around you. But there are two assumptions that can be made: 1) You follow people who say things that interest you, and 2) Events of significance often peak within groups. By organizing hashtags among people you follow, it’s easy to develop a personalized trend graph that refreshes every 15 minutes or so. That means instead of having to pour through dozens or hundreds of tweets to see what’s happening – you can merely glance at an ordered list of top-hits.

Translating this to Your Business

You likely have an overwhelming amount of data pouring in on any given day. Continue reading Opportunities for Data Innovation are All Around Us

The ALPAC Sales Methodology

I want to share a quick bit about a sales process / methodology that I’ve found to be invaluable – and I’ve had to train people dozens of times. It is a helpful framework for both sales and marketing professionals because it covers the life-cycle of customer on-boarding. In simplest terms, the process is this: ALPAC. Audience, Lead, Prospect, Account, Customer.

Here are the sales & marketing stages, broken down with greater detail.


This is fundamentally a Marketing stage. Audience comprises everyone who isn’t yet in your sales funnel. The Audience can really be broken up in to 2 groups: Audience we want to reach, and Audience we don’t care about reaching. Audience converts to the next stage by progressing those people through the AIDA marketing process: Attention, Interest, Desire, Action. I’m going to write more in the near future about the importance (and measurability!) of AIDA in social media campaigns, but for now just suffice to say that the general population needs to become aware of your product / service / business, become interested, gain desire, and finally, take action. Depending on the nature of your product, that action is typically self-designation as a person who wants more information – and turns themselves in to a lead. Continue reading The ALPAC Sales Methodology

Social Mindshare

As a general rule of thumb, you should be building your brand around a single word or extremely short phrase to create mindshare in your audience. This isn’t a slogan. Slogans might be part of it. But the simple fact of the matter is that your audience is being bombarded on a daily basis by hundreds – if not thousands – of brand and marketing messages. Capturing and solidifying a single word or phrase is crucial. Nike has spent decades building itself in to synonymous with “sports.” Alternatively (and perhaps this is just my own personal connection – and that’s part of the beauty of it), when I think of Adidas – the first thing that comes to mind is “Soccer”. In another direction, the Underarmor brand to me represents “Football clothes”. All of these companies are direct competitors in many fronts – but within my mind – this is the mindshare that they’ve eached achieved.

The same thing is true amongst car brands. I’m an Audi driver, so in my mind they captured “Sport Luxury” in my mind. BMW I’m sure would be ticked off because that’s a mindshare that they’ve gone after. But the beauty of branding and mindshare is that it happens in the mind of the recipient, not the sender.

What do you think of when I describe the comparison between iPhone, Android, Nokia, and RIM? iPhone might spark “Innovator and Easy”, Android might spark “Open Cool”, Nokia might spark “Cheap phones” and RIM might spark “Relic” (sorry RIM). Those are my perceptions. That’s the mindshare that those brands occupy in my mind today. It can change; but often not by anything the company itself does. It has a great deal more to do with the reputation, conversation, media & interpersonal connections, etc. For instance, I know far more people with iPhones – so my conversations with other people tend to focus on topics like “Check out these cool apps I have” or “I love it how easy it is to…” Whereas my friends with Blackberries languish with phones that appear to be unable to do much of anything contemporary and they complain that they wish they could change their phones (but their company is stuck on the platform). Continue reading Social Mindshare

The Shifting Social Landscape

Building a digital “home” in the social landscape is much like building a physical home – on quicksand. If you don’t believe me – let’s look at some of the trends that have happened over the summer…

Facebook’s IPO Woes

Let’s face it – Facebook insiders played the market like a well-tuned guitar. All the insiders got in on the action pre-IPO, and the retail investors were buying their exits during the IPO (and as insider shares become “unlocked” like Peter Thiel’s). But more concerning is the underlying challenge to value a social media company.

Remember – and this is important – in the social media space, the “users” are not the “customers“. Continue reading The Shifting Social Landscape

Google Should Make a CMS… Right Now.

I’ve been thinking about this a little bit over the last couple days, and I’ve come to this conclusion. Google should be making a Content Management System (CMS). Right now.

I’m not talking about their existing website product, Google Sites. That’s just a Google version of Geocities, with less dancing babies. No, what I’m talking about is a full-blown WordPress, Drupal, Joomla competitor. They have the capability to do it, and they DEFINITELY have the incentive.

“What was traditional site content of the past decade – essays, posts, pictures, etc. is now moving away from open.”

Look at the modern web through Google’s eyes. It’s fragmenting. What was traditional site content of the past decade – essays, posts, pictures, etc. is now moving away from open. Obviously Google’s biggest threat is Facebook – and now that they’re a public company, the shareholders are going to nudge the company to embrace more open competition to Google directly. Continue reading Google Should Make a CMS… Right Now.

The Freelance Life (Part 2)

So this post is a follow-up to my article yesterday – My (Simple) tips for Freelancing. I wanted to go collect some more ideas to share that I think can amplify the conversation beyond just my basic ideas. There are so many people freelancing and calling their own shots these days that there’s plenty of interesting insight to be found.

… The Couch is Calling …

One of the best / worst parts about freelancing definitely has to be when you’re not running at 100%… The upside is exactly what Michelle mentioned here – you can just post on the couch and tinker. The downside? You’re responsible for your own healthcare. Definitely a mixed bag – but believe it or not self-coverage isn’t that expensive. Gets a lot more pricey if you’re covering kids / family – but it’s still pretty reasonable.

The downside of Freelancing is that if you’re not focused on projects – it can be really easy to get distracted by things at home. Of course – anyone who’s been in a corporate environment knows that an office is full of distractions too!

Dude – I love this. That’s so true. Freelancing is definitely a legitimate enterprise, but older generations sometimes look at the online business world as a bunch of smoke & mirrors (and spammers). Sometimes it takes a good conversation with the family to really show & share what you’re up to. Great point Salman.

That’s another thing often overlooked in freelancing… You really have to do everything by hand. There’s no “mail room” no shipping supplies, and you gotta foot the bill for all the postage. Direct mail (especially like pointed out here) is so effective if you’ve got an engaged client / prospect base, but it can add up really quickly. Look for deals on shipping products when you can – Staples or Office Depot usually have clearance racks for shipping supplies that can save you a ton of money on envelopes, packing material, and even weird-sized shipping boxes. If you’re sending more than a dozen pieces of mail a week, I definitely recommend checking out Stamps.com or similar print-stamps-from-home solutions.

There’s definitely some truth to this. Freelancing IS very similar to being an employee, since your clients will often place similar demands on you as they would an internal employee. Though if you prove your expertise, I think you can often establish more of a peer-to-peer relationship, rather than a client-vendor one. It’s tricky, but quite possible – especially if you’re providing skills that truly support the clients’ business that they don’t have internally.

Had to include Alexanders’ response, because it’s absolutely part of the reality too. Like I’d written before – the project & the client selection process is so crucial! If you find clients who are looking for skilled service providers to help amplify their business and meet their goals – it feels much less like an employee relationship and much more like a pair of business professionals working together towards a common goal.

And finally, I think Brian has conveyed what many freelancers feel after a period of time. There are two worlds when it comes to freelancing: People who freelance because they want the freedom, independence, and ability to call their own shots. They typically leave stagnant work environments to strike out on their own. Then there are also freelancers who are doing it because the job market is rough.

Thanks for reading! Again – if you want to check out the original post check out My Tips for Freelancers.

My Tips for Freelancing

A friend wrote this question, and I just felt like it was good blog-fodder…

When dealing with clients, whats the best way to set time restrictions for yourself so you can have a social life or be able to hangout with your kids? Are stating you have a hardstop later in the day the wrong way to go about it? What if something comes up? I’m conflicted going from a 9-5 office gig to working for multiple clients from home.

Dude. I have so many opinions on this.

Freelance Clients aren’t Corporate Clients

Freelance clients come in every variety – so be forewarned. Even the most stable-sounding client could turn in to a nightmare headcase if you’re not paying attention.

For starters, I’d suggest you pick clients who share your value system. If you believe that a work day should start and stop at certain times, make that part of your client onboarding process. Ask them when they expect deliverables from you – morning, afternoon, evenings, weekends?

Secondly, make sure your clients understand your circumstances (to a degree). If you set aside 4-8pm each evening as “playing with the kids time” make sure your client understands that ahead of time.

Also, especially in this economy – cashflow is king. If a client is asking for payment terms or flexibility in paying for services, either decline them or make them one of your “when I’ve got the time” clients. You should have 2 classes of clients: Those who are paying the full run rate – so you better get running! … and those paying the “jog” rate – where you just have to get to the end eventually, no sprinting required.

Just remember – there’s a reason why your client will consider you rather than a corporate alternative. What would inspire your confidence if you were in their shoes? What would you be willing to accept? Typically, they want a freelancer because they can get more for less, and often (in creative industries) a much more dynamic set of ideas. But just realize part of that proposition is that they expect to be able to demand your time under certain circumstances. Just be clear up front what you think is fair. Continue reading My Tips for Freelancing