What types of management problems plague startups?

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Being an avid reader of Fred Wilson’s AVC, I’ve learned much over the years. And one thing he underscores is that *ideas* are a dime a dozen. And that great investments are in team & execution.

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As a long time consultant, I’ve had the good fortune to see a lot of startups under the microscope. If you work a FT role for 2 years, over a decade you may work at 5 companies. In the same amount of time, i’ve worked at over 65 companies.

In those years I’ve encountered great teams that are super organized, and continue to move the product forward. But I have also seen a number of symptoms, that caused the business problems, and slowed down their march forward.

Low morale

One firm I worked at a few years back was in the space around education, specifically with a lot of microlearning products, with big customers doing corporate onboarding.

Their sales team was world class, closing bigger and bigger deals, but engineering had terrible and festering problems. As it went, they grew to have hundreds of employees in a matter of a year or two. Meanwhile the CTO was not a big people person. He didn’t like speaking in front of large groups, nor was he very hands on. As a small ten person startup he was super technical and talented, but as the company grew so fast, it left a leadership vacuum.

And then some bad hires grew the engineer team fast. But internally there was a lot of infighting. The original founding team worked hard and had strong direction, but the new hires all vied for control. And the ugly personalities reared their heads.

After a few short weeks, half the engineering team quit, in a matter of days. A tough blow to a team already struggling to keep up with growth.

It is not easy to right a large plane in mid flight like that, carrying plenty of technical debt besides.

Related: A CTO must never do this

Bad alignment

Another place I had the pleasure of working at was a well known digital media brand, that expanded into film production, recording and even investigative reporting. For all it’s wide ranging efforts, it presided over a huge growth business, with seemingly unlimited revenue. Impressive to be sure.

On the technology side, however things were not so sunny. As their business grew, they planned to consoldate data from many disparate divisions. And this is a process that many growing businesses go through. Finance in one platform & database, bookings & production in another, while analytics and viewer statistics in yet a third. But how to report on all of that data?

As a special crack team of big data experts, we were assigned the task of building out this centralized repository of business truth. And as we built and architect that system, we needed to work closely with the operations division.

Now in this business, they were using public cloud, Amazon Web Services like many other startups. However they had a separate team of devops who presided over these accounts.

As our team was handed strict deadlines to deliver working reports & systems, we had conference calls with the Devops team. However that team was not on board with those deadlines. They pushed back and claimed such systems would take months to setup.

As we explained expectations being pushed on our shoulders, Devops said “just push back and say no”. They advised that we “send it back up the chain”

But what if there’s a chink in the chain?

Clearly the two teams were not aligned at all on deadlines & deliverables. And that’s not a fault of either of those teams. It straightaway falls in the lap of management to align those.

And we were somehow stuck in the middle. Ugh!

Related: How to avoid legal trouble in consulting

Loose discipline

One startup I worked at had a security and authentication app.

Here teams were fairly happy on the whole. In fact they raved about having a great boss. Indeed the boss was a very kind leader, understanding, patient, and hardworking.

However, over and over, we lacked a “decider”. Here other team members were giving each other tasks. Promises were made loosely, and then forgotten one or two weeks later. And a constant lack of direction dragged down delivery.

For my money, a promise to have a meeting at 10am, is one all parties should abide. Whatever their level in the business. Not be late, have excuses about trains, or simply skip the meeting with no explanation. These types of habits cause the team to grow weary, and lower the bar of expectations.

Frustrating indeed.

Related: When you have to take the fall

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30 Days of Aspirin for your Ailing Management Headaches

Take Two & Call Me In the Morning

I like a book like Gerry Czarnecki’s even if I can’t pronounce his name. He’s laid out things for readers, a very busy bunch who are going to have trouble finding time in their day to read, but can sorely use the advice. Organized into 30 daily bites of probably 15-20 minutes, you can dig through on your commute to work, or on your lunch break.

Also check out Who Moved My Cheese a business self-help classic.

Czarnecki should know. As a 2nd Army Lieutenant then later heading up board of directors at organizations large and small he’s seen a lot. He digs up the best stories, and offers up lessons straight out of his experiences.

[quote]
On interviews – Be careful that you do not let the resume dominate your conversation. You will gain better insight if you listen to what the candidates want to talk about or what they think you want to talk about. – Gerry Czarnecki
[/quote]

Some of the topics you’ll touch on…

o dealing with mistaken hires that don’t work out
o finding a mentor
o career moves & pivots
o setting expectations with new hires
o hitting peak performance
o filling your bus with rock stars

For startups an all-time favorite of mine is REWORK – 37 Signals guys. These guys have taken the lean methodology and built a real business by being efficient. The pages resonate for me as a small business owner. I’ve found many of the same lessons work in the real world for me.

[mytweetlinks]

Also read
Thank you for arguing by Jay Heinrichs
. With some of the best advice on rhetoric, sales, presentations & persuasion, I re-read bits of the book often.

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Consulting essentials: Managing & Completing Engagements

This is the second in a series of three articles on Consulting Essentials.
Read the previous post, Consulting essentials: Getting the business

Communicating well and knowing when to step in or stand back is the linchpin of successful consulting.
Some people have natural charm. If you’re one of these people you’ll find consulting is definitely for you. You’ll use that skill all the time as each new client brings a half dozen or a dozen new people to interact with.

If it doesn’t come easily, practice practice practice. Try to get out of your own head space, and hear what troubles your client, and what big business challenges worry them.

Be ready to help but don’t try to be the hero


A decade ago I worked for an Internet startup. They were having serious performance problems which was slowing down the site, and turning users away. When digging into the systems I found serious security issues besides the performance ones, and got distracted trying to wrap up those lest someone break in and destroy or steal their business assets. Communicating the situation to the client, they looked aghast. After explaining the situation to them, they understood the risks and explained that the current priorities were to get users back online.

The technical problems I saw may not have been aligned with the business priorities. Your job is to make your client happy. Provide your professional opinion and advice whenever and wherever your skills come into play, but let them run their own business.

If you’re focusing on one area, and you discover other problems or things that may need resolving going forward, bring this to the attention of the client. Allow them to prioritize for themselves. It’s their business not yours. Your job is to give your professional opinion, raise concerns that you see, but most importantly solve problems they want you to solve.

Project Your Personality

Smile a lot and listen to people. Make sure you’re talking less than half the time. When you first engage with a client, they should be speaking more like two-thirds of the time. You want to get in the habit of listening, and stepping in your clients shoes. You want to understand their pain, their business concerns and how to satisfy them.

Manage Time Efficiently

Get things done. Everybody talks about it, but not everyone does it. I personally avoid all the faddish tools for this, and use a simple checklist. Focus on the task at hand. Give yourself a doable list of tasks each day, and check them off as you go. Try hard to avoid working on things not on that list. The last point relates back to the principle of solving only the problems that you’ve been asked to solve.

Communicate Successes & Progress

In many engagements you’ll come upon struggles and get blocked by situations that seem intransigent. I can’t emphasize enough how important it is to communicate with the client during these situations. Don’t get stuck thinking it will make you look weak. Communicating with the client has a number of surprising advantages.

For one sometimes they’ll have a solution, such as a different angle on the business problem, or insight and details that just simplify the problem you think you thought needed to be solved.

Second, it allows the client to adjust schedules in advance if something will take a little longer. You’d be surprised how often a client will sympathize with a difficult problem.

Lastly, involving the client intimately allows them to enjoy the triumph when you solve the problem. This helps morale, communicates more about what it is you do day-to-day and how you work through a problem. And overall it helps them appreciate the intrinsic value you’re providing.

Don't be that guy–Social tips for geeks

Sheldon CooperAs a tech consultant one of the most interesting parts of the job is being able to observe human relations at work. I’ve learned through the years that because tech people and non-tech people speak different ‘languages’, bridging the communication gap is a critical part of my role as a consultant.

Sometimes the relationship between tech and other business units is less sweet. The typical complaints are that IT guys are always denying requests, aloof and even downright unhelpful.

On the other side, the geeks feel frustrated that people “just don’t listen”. We remind people to always use strong passwords, and people still make “password” their password. We train end-users and give specific guidance and instructions but they still commit the fundamental mistakes. Meanwhile, the managers expect IT staff to perform miracles.

So who can be blamed when this animosity exists? Geeks for their arrogance? Or end-users for not making an effort to improve their understanding of tech concepts? Perhaps both sides can share the blame. But as tech folks we can try to make things better by working on our communication skills. Sliding into aloofness will not only make people resentful but suspicious of our motives too. Don’t be that guy!

If you’ve found yourself slipping up in the people-skills department, here are a few tips that can help you along. Think of understanding and persuading other people as a puzzle equally complex as the biggest engineering challenge. In that light you can look at it as an ongoing project to improve your communication and charm.

  1. Please Speak My Language
  2. Martha Stewart said “the biggest mistake people make is they expect that others know stuff…”. Amen Martha. In my experience a lot of folks fall into this category. Ever been at a meeting where financial folks are waxing on about the business bottom line, margins, and shareholder value? If talk of capex, opex and other financial terms confound you, then you know the feeling. So why subject others to this when we talk tech? There’s no reason to, and people will love you for using a language that everyone can understand. Use analogies and stories to emphasize an idea or point so it resonates with your audience.

  3. Listen to me
  4. Everyone wants to be listened to; hopefully that’s obvious. But sometimes we get stuck on our own ideas, and focus more on people hearing us. It may sound counterintuitive, but psychologically speaking, listening more to the other person makes them listen to your ideas more. Start by giving plenty of time to speak, and try to repeat the other persons ideas in your own words. You’ll set the tone for a more reasoned dialogue and find your own thoughts heard more too.

  5. Be more positive
  6. Perhaps it is our engineering backgrounds, and the discipline that the scientific method ingrains in us. You may think that being critical is a common way to approach a discussion on issues. However this may come across as negative and stand-offish depending on how you communicate. What’s more if your audience doesn’t see things from your perspective, you may find yourself complaining and condemning proposals.

    Better to find the positive as a common starting point. Speak about all the things that work well first, before working your way around to points of difference.

  7. Speak slowly
  8. Psychologists have found that people sense more confidence and listen more to people who speak slowly. It may seem counterintuitive, after all if you speak quicker, you may be able to get that complicated idea out into the world before you are ever interrupted! What’s more speaking slowly allows you to think about what might come next, anticipating reactions, or even changing direction slightly in mid-stream. It also allows you more time to catch what might be a … or a slip of the tongue.

  9. A few more ideas to chew on…
    1. Smile more
    2. You may not be aware of how often you’re smiling or not. What’s more you may think it insincere to try to smile. But a frown, or other negative face can criticize your audience as much as actual words can. And it can set people off on the wrong foot, so they won’t listen to you either. Better to stay positive, and convey that with a smile.

    3. Remember & use people’s names
    4. People love to hear their own names. Remembering and using someone’s name improves the chances that they will listen to you and your ideas.

    5. Repeat what others say in your own words
    6. This one is really crucial. By repeating someone’s ideas in your own words you do a few things all at once. First you improve communication, as it is so often the case that we misunderstand someone else’s ideas, repeating them in your own words allows them to hear how you’ve digested their point, and allows them to comment or adjust if you missed something. It also shows them you are really listening. If you’re going to critique someone, and they feel you didn’t really get their idea, they’ll be very unlikely to listen.

    7. Try not to say “you’re wrong”
    8. Even in the cases where the other person is completely wrong, this statement may not have the intended affect. It may simple cause them to wall off and not listen to you. Better to point out the sides of what they are saying that you can agree with first, then come around to some differences.

    9. Read Dale Carnegie
    10. The classic book “How to Win Friends & Influence People” should really be required reading for the geek set. Being personable and charming may not be natural to all of us, but a lot of it can be learned with practice. Dale Carnegie has written a sort of bible on the topic, and it’s definitely worth a read.