Great Mistakes in Technical Leadership – reprint

Great Mistakes in Technical
Leadership
11 Jun 2006

Originally:
Hacknot – Great Mistakes in Technical Leadership

http://www.hacknot.info/hacknot/action/showEntry?eid=87

but that site is now gone. I found this text in Google cache and took liberty of posting it here.

“ If you are a good leader who talks little, they will
say when your work is done and your aim fulfilled,
“We did it ourselves.””
Lao-Tse, cited in 1

Perhaps the most difficult job to do on any software
development project is that of Technical Lead. The
Technical Lead has overall responsibility for all technical
aspects of the project – design, code, technology
selection, work assignment, scheduling and architecture
are all within his purview. Positioned right at the border
of the technical and managerial, they are the proverbial
“meat in the sandwich.” This means that they have to be
able to speak two languages – the high-level language of
the project manager to whom they report, and the
low-level technical language of their team. In effect,
they’re the translator between the two dialects.
Observation suggests that there are not that many senior
techies who have the skills and personal characteristics
necessary to perform the Technical Lead role well. Of
those I have seen attempt it, perhaps ten percent did a
good job of it, twenty percent just got by, and the
remaining seventy percent screwed it up. Therefore most
of what I have learnt about being a good Technical Lead
has been learnt by counter-example. Each time I see a
Technical Lead doing something stupid, I make a mental
note to avoid that same behavior or action when I am
next in the Technical Lead role.
What follows is the abridged version of the list of
mistakes I have assembled in this manner over the last
thirteen years of watching Technical Leads get it wrong.

It is my contention that if you can just avoid making
these mistakes, you are well on your way to doing a good
job as a Technical Lead. You might consider it a
long-form equivalent of the Hippocratic Oath “First do
no harm,” although given the self-evident nature of
many of these exhortations, it is more like “First do
nothing stupid.”

Mistake #0: Assuming the team serves you
Perhaps the most damaging mistake a Technical Lead
can make is to assume that their seniority somehow
gives them an elevated status in their organization. Once
their ego gets involved, the door is open to a host of
concomitant miseries such as emotional decision
making, defensiveness and intra-team conflict.
I can’t emphasize enough how important it is to realize
that although the Technical Lead role brings with it
many additional responsibilities, it does not put you
“above” the other team members in any meaningful
sense. Rather, you are on an exactly equal footing with
them. It’s just that your duties are slightly different from
theirs.
If anything, it is you that is in service of them, given that
it is part of your role to facilitate their work. To put it
another way, you are there to make them look good, not
the other way around.

Mistake #1: Isolating yourself from the team
In some organizations, having the title of Technical Lead
gives you entitlements that the rank and file of your team
do not enjoy. Sometimes, the title is considered
sufficiently senior to entitle you to an office of your own,
or at least a larger workspace if you must still dwell in
cubicle land.
It is a mistake to take or accept such perquisites, as they
serve to distance you (both physically and
organizationally) from the people that you work most
closely with. As military leaders know, it creates an
artificial and ultimately unhealthy class distinction
between soldiers and officers if the latter are afforded
special privileges. To truly understand your team’s
problems and be considered just “one of the guys”
(which you are), you need to be in the same
circumstances as they are.

Mistake #2: Employing hokey motivation
techniques

Different sorts of people are motivated by different sorts
of rewards. Programmers and managers certainly have
very different natures, yet it is surprising the number of
managers and aspiring managers who ignore those
differences and try to reward technical staff in the same
way they would like to be rewarded themselves.
For example, managers value perception and status, so
being presented with an award in front of everyone, or
receiving a plaque to display on their wall where
everyone can see it, may well be motivating to them.
However programmers tend to be focused on the
practical and functional, and value things that they can
use to some advantage. Programmers regard the sorts of
rewards that managers typically receive as superficial
and trite. They have a similar view of “team building”
activities, motivational speeches and posters and the
like.
So if you want to motivate a developer, don’t start
cheering “Yay team” or force him to wear the team t-shirt
you just had printed. Instead, give him something of use.
A second monitor for his computer will be well received,
as will some extra RAM, a faster CPU, cooler peripherals,
or a more comfortable office chair. It’s also hard to go
wrong with cash or time off.
Developers are also constantly mindful of keeping their
skill sets up to date, and so will value any contribution
you can make to their technical education. Give them
some time during work hours to pursue their own
projects or explore new technologies, a substantial
voucher from your local technical book store, or leave to
attend a training course that interests them – it doesn’t
have to be something that bears direct relationship to
company work, just as long as it has career value to
them.
Mistake #3: Not providing technical
direction and context

A common mode of failure amongst Technical Leads is
to focus on their love of the “technical” and forget about
their obligation to “lead.” Leading means thinking ahead
enough that you can make informed and well-considered
decisions before the need for that decision becomes an

impediment to team progress.
The most obvious form of such leadership is the
specification of the software’s overall architecture.
Before implementation begins, you should have already
considered the architectural alternatives available, and
have chosen one of them for objective and rationally
defensible reasons. You should also have communicated
this architecture to the team, so that they can always
place the units of work they do in a broader architectural
context. This gives their work a direction and promotes
confidence that the teams collective efforts will bind
together into a successful whole.
A Technical Lead lacking in self-confidence can be a
major frustration to their team. They may find
themselves waiting on the Lead to make decisions that
significantly effect their work, but find that there is some
reticence or unwillingness to make a firm decision.
Particularly when new in the role, some Technical Leads
find it difficult to make decisions in a timely manner, for
they are paralyzed by the fear of making that decision
incorrectly. Troubled that a bad decision will make them
look foolish, they vacillate endlessly between the
alternatives, while their team mates are standing by
wondering when they are going to be able to move
forward. In such cases, one does well to remember that a
good enough decision now is often better than a perfect
decision later. Sometimes there is no choice amongst
technical alternatives that jumps out at you as being
clearly better than any other – there are merely different
possibilities, each with pros and cons. Don’t belabor such
decisions indefinitely. In particular, don’t hand over such
decisions to the team and hope to arrive at some
consensus. Such consensus is often impossible to obtain.
What is most important is that you make a timely
decision that you feel moderately confident in, and then
commit to it. If all else fails, look to those industry
figures whose opinions you trust, and follow the advice
they have to give.
Finally, always be prepared to admit that a decision
you’ve made was incorrect, if information to that effect
should come to light. Some of the nastiest technical
disasters I’ve witnessed have originated with a senior
techie with an ego investment in a particular decision,
who lacks the integrity necessary to admit error, even
when their mistake is obvious to all.

Mistake #4: Fulfilling your own needs via
the team

You will occasionally hear people opine that one should
not let the personal interfere with the professional. In
other words, difficulties at home should not interfere
with the execution of duties in the workplace. In some
environments, the obvious expression of emotion is
simply taboo. But such ideas don’t mesh with reality too
well. People are holistic creatures and our life experience
is not so conveniently compartmentalized, no matter
how desirable some Taylorist ideal may be.
Just the same, there are practical and social limitations
upon workplace behavior which some may be tempted to
flaunt, to the discomfort and embarrassment of their
colleagues. The broader one’s influence, the greater the
opportunity to co-opt activities that should be focused on
work, and turn them to personal effect.
For example, meetings (complete with buffet) make a
fine social occasion for those not concerned with making
best use of company time. Team-building exercises
provide an easily excused opportunity to get away from
the office and out into the sun, as do off-site training
courses and conferences.
Pair programming seems to be most appealing to those
who like to chat about their work … continually. An
excessive focus on group consensus-based
decision-making for all technical aspects of the project,
even the trivial ones, may be a sign that a Technical Lead
is more concerned with the sociology of the project and
their place amongst it, than with leadership and making
efficient use of people’s time and effort.

Mistake #5: Focusing on your individual
contribution

Changing roles from developer to Technical Lead
requires a certain adjustment in mindset. As a developer
you tend to be focused upon individual achievement.
You spend your time laboring on units of work, mainly
by yourself, and can later point to these discrete pieces of
the application and say, with some satisfaction, “I did
that.”
But as a Technical Lead your focus shifts from individual
achievement to group achievement. Your work is now to

facilitate the work of others. This means that when
others come to you for help, you should be in the habit of
dropping everything and servicing their requests
immediately. A fatal mistake some Technical Leads make
is to try and retain their former role as an individual
contributor, which tends to result in the Technical Lead
duties suffering, as they become engrossed in their own
problems and push the concerns of others aside.
The constant alternation between helping individuals
with low-level technical problems and thinking about
high-level project-wide issues is very cognitively
demanding. I’ve come to call the problem “zoom fatigue”
- the mental fatigue which results from rapidly changing
between the precise and the abstract on a regular basis.
It’s like the physical fatigue that the eye experiences
when constantly switching focus from long distance to
short distance. The muscular effort required within the
eye to change focal length eventually leads to fatigue,
making the eye less responsive to subsequent demands.
Similarly, you get cognitive fatigue when in one moment
you are helping someone with an intricate coding issue,
and in the next you’re examining the interaction between
subsystems at the architectural level. The latter requires
a more abstract mental state than the former, and
alternating between the two is quite taxing.
As a result, people may come to you seeking help with
something that has been the sole focus of their attention
for several hours or days, and you will find it difficult to
“task switch” from what you were just doing into a
mindset where you can discuss the problem with them
on equal terms. I find it helpful to just ask the person to
give me ten minutes to get my head into the problem
space, during which I might retreat to my own machine
and study the problem body of code in detail, before
attempting to help them with it.

Mistake #6: Trying to be technically
omniscient


Just because you have the last word in technical
decisions, don’t think that it is somehow assumed that
you are the programming equivalent of Yoda. With the
variety and complexity of development technologies
always growing, it is increasingly difficult to maintain a
mastery of any given subset of that domain. As in most
growing fields, those who call themselves “expert” will
progressively know more and more about less and less.

It is therefore entirely possible that you will be learning
new technologies at the same time as you are first
applying them. The mistakes you make and the gaps in
your knowledge will be abundantly obvious to your team
members, so it is best to abandon at the outset any
pretext of having it all figured out.
Be open and honest about what you do and don’t know.
Don’t try and overstate or otherwise misrepresent the
extent and nature of your familiarity with a technology,
for once you are found out, the trust lost will be very
difficult to regain.
There is an opportunity here to widen the knowledge and
experience of all team members. You might like to
appoint certain people as specialists in particular
technologies, giving them the time and task assignments
necessary to develop a superior knowledge of their
assigned area. To avoid boredom and unnecessary risk,
be sure to give these resident experts plenty of
opportunity to spread their knowledge around the team,
and to exchange specialties with others.
Adopting this “collection of specialists” approach makes
it clear that you are not presuming to be all things to all
people; and that you have faith in the abilities of your
colleagues. But it will require you to park your ego at the
door and be prepared to say “I don’t know” quite
frequently.
But be careful not to lean on others too heavily. It is still
vitally important for you to have a good overarching
knowledge of the technologies you are employing,
particularly those elements of them that are critical to
their successful interoperation in service of your systems
architecture.

Mistake #7: Failing to delegate effectively
To successfully lead a group, there must be an attitude of
implicit trust and assumed good intent between the
leader and those being lead. Therefore a Technical Lead
must be willing to trust his team to be diligent in the
pursuit of their goals, without feeling the need to watch
over their shoulder and constantly monitor their
progress. This sort of micromanagement is particularly
loathed by programmers, who recognize it as a tacit
questioning of their abilities and commitment.
But ineffective delegation can also arise for selfish

reasons. Several times now I’ve seen Technical Leads
who like to save all the “fun” work for themselves,
leaving others the tedious grunt work. For example, the
Technical Lead will assign themselves the task of
evaluating new technologies, constructing exploratory
and “proof of concept” prototypes, but once play time is
over and the need for disciplined work arrives, hand over
the detailed tasks to others.
Not only is effective delegation desirable with respect to
team morale and project risk, on large projects it is
simply a necessity, as there will be too much information
to be managed and maintained at once for one person to
be able to cope.

Mistake #8: Being ignorant of your own
shortcomings

Some people simply don’t have the natural proclivities
necessary to be good Technical Leads. It’s not enough to
have good technical knowledge. You must be able to
communicate that knowledge to others, as well as
translate it into a simpler form that your management
can understand.
You also need good organizational skills. Coordinating
the efforts of multiple people to produce a functionally
consistent outcome is not easy, and demands a
methodical and detail-oriented approach to planning
and scheduling. If you can’t plan ahead successfully, you
will find yourself constantly in reactive mode, which is
both stressful and inefficient.
If you don’t have these qualities naturally, you may be
able to develop them to some extent, through training
and deliberate effort. But it may ultimately be necessary
for you to lean on others in your team to support you,
should they have strengths in areas in which you have
weaknesses.

Mistake #9: Failing to represent the best
interests of your team

Perhaps the most nauseating mistake a Technical Lead
can make is to become a puppet of the management
above them. As the interface between management and
technicians, it is the Technical Lead’s role to go into bat
with their management to represent the best interests of
their team. This means standing up to the imposition of
unreasonable deadlines, fighting for decent tools and

resources, and preventing the prevarications of
management from disturbing the rhythm of the project.
A weak-willed or easily manipulated Technical Lead will
incur the disrespect of his team.
Unfortunately, such spineless behavior is quite common
amongst the ranks of the ambitious, and you don’t have
to look far to find obsequious Technical Leads who will
gladly promise the impossible and impose hardship on
their team, in the interests of creating a “can do” image
for themselves.
Mistake #10: Failing to anticipate


An essential part of the Technical Lead’s role is keeping
an eye on the “big picture” – the system-wide concerns
that are easily forgotten by programmers whose
attention is consumed by the coding problem they
currently face.
These “big picture” issues include those non-functional
requirements sometimes called “-ilities” -
maintainability, reliability, usability, testability and so
on. If you don’t make a conscious effort to track your
progress against these requirements, there is a high
probability of them slipping through the cracks and
being forgotten about until they later emerge as crises.
If you don’t have a dedicated project manager, it may
also fall to you to handle the scheduling, tracking and
assignment of tasks. It isn’t uncommon for Technical
Leads to find themselves playing dual roles in this
manner. You may not be very fond of such
“administrative” duties, but their efficient performance
is critical to the smooth running of the project, and for
the developers to know where they are and where they’re
going. Don’t make the mistake of ignoring or devaluing
these tasks simply because they are non-technical in
nature.
Mistake #11: Repeat mistakes others have
already made

It is common for developers to dismiss the experience
reports of others as having no relevance to their own
situation. Indeed, it is wise to approach all anecdotal
evidence with skepticism. But it is unwise to completely
disregard the advice of others, particularly when it is
accompanied by sound reasoning, or can be
independently verified. Ignoring good advice can be very

expensive; it is said that “Experience keeps a dear school
but fools will learn in no other.”
The unwillingness of developers to learn from the
mistakes of others, and the ease with which you can
encounter software project horror stories in the
literature and recognize your own projects in them, is
evidence suggesting that the software industry as a
whole is not getting any wiser.2 You need not contribute
to that collective stupidity.

Mistake #12: Using the project to pursue
your own technical interests

Remarkably, developers can reach quite senior levels in
their organization without having learnt to appreciate
the difference between work and play. Many are
attracted to programming to begin with because, as
hobbyists, they enjoyed fooling around with the latest
and greatest technologies. Somehow they carry this
tendency to “play” with technologies into their working
lives, and it becomes the aspect of their jobs that they
value most. From their perspective, the purpose of a
development effort is not to create something of value to
the business, but to create an opportunity to experiment
with new technologies and pad their CV with some new
acronyms.
Their technology selection is based upon whatever looks
“cool”. But a rational approach to technology selection
may yield quite a different result to one guided by
technical enthusiasm or a fascination with novelty. New
technologies are often riskier choices, as the
development community has not had much time to apply
the technology in varying circumstances and thereby
discover its weaknesses and shortcomings. Putting an
immature technology on a project’s critical path is
especially risky. So an older, tried and true technology
may be a more rational choice than a new, unproven one.

Mistake #13: Not maintaining technical
involvement

In order to fully appreciate the current status of the
project as well as the difficulties your team is facing, it is
vital that you maintain a coding-level involvement in the
project. If you’re not cutting code, it is too easy to
become divorced from the effects of your own decision
making, and to be seen by other developers as being out
of touch with the technical realities of the project.

Mistake #14: Playing the game rather than
focusing on the target


In some organizations, being a Technical Lead is a
politically sensitive position. Technology choices, work
assignments and project outcomes are all just tools to be
used in the pursuit of personal agendas. To some, this
“game” of political influence is both fascinating and
addictive. They play it in the hope of gaining some
advantage for themselves, and do so to the detriment of
the project and the individuals upon it. When they don’t
have their eye on the ball like this, devoting more energy
to Machiavellian maneuverings than to the technical
difficulties of the project, then the project inevitably
suffers.

Mistake #15: Avoiding conflict

Many people find interpersonal conflict distasteful.
Some dislike it so much that they will do practically
anything to avoid it, including giving up in technical
disputes. Such people are prone to being walked over by
those more aggressive and forthright.
This is bad enough for the individual, but worse if that
person is meant to be representing the best interests of a
team. A meek Technical Lead can be a real liability to a
development team, who will find themselves buffeted
about by external forces that they should have been
shielded from, and burdened by demands and goals that
are not informed by the project’s reality.
With such a disposition, a Technical Lead may be unable
to even deal effectively with unruly behavior or
inadequate performance from members of their own
team.

Mistake #16: Putting the project before the
people

It’s one thing to be focused on the project’s goals, but
quite another to adopt a “succeed at all costs” attitude.
Ambitious Technical Leads, concerned with the image
they project to their management, sometimes accept
impossible goals or unreasonable demands, because they
lack the courage or integrity to say “no.” These goals then
become the development team’s burden to shoulder,
leading to increased stress, higher defect injection rates,
longer working hours and lower morale. There is a
tendency to be so focused on the end goal that the effects

of the project on the developers gets overlooked. It is not
uncommon for successful delivery on a high pressure
project to be followed by the resignations of several
disgruntled team members, making the project’s
triumph a pyrrhic victory indeed.
Given the costs of hiring and training staff, treating
developers as expendable resources makes no financial
sense, quite aside from the ethical implications of such
treatment. A wise Technical Lead will know that putting
the well-being of the developers first also produces the
best results for the project and the business. Project
success should leave the participants satisfied with their
achievement, not burnt out and demoralized.
Mistake #17: Expecting everyone to think
and act like you

Being a Technical Lead may be the first time you are
exposed so frequently and directly to the problem
solving styles and low-level work habits of others.
Programming is traditionally an individual activity.
Programmers are often able to face the technical
difficulties of their work in isolation, emerging sometime
later with the completed solution. But as a Technical
Lead you will frequently be called on to help those who
are stuck part way through the problem-solving process,
unable to proceed. Seeing a solution that is “under
construction” might be a bit of a shock to you at first, as
you may find your colleagues approach to problem
solving dramatically different to your own. Some people
work “outside in”, others “inside out”, others jump all
over the place, some work quickly with lots of trial and
error, others slowly and methodically. It is tempting to
stand in judgment of approaches and methods that don’t
gel for you, pronouncing them somehow inferior. Avoid
the temptation. Learn to accept the varieties of cognitive
styles on your team, and recognize that this cognitive
diversity may actually be an asset, for the variety of
perspective it brings.
Mistake #18: Failing to demonstrate
compassion

Although I’ve put this last, it is in some ways the most
important of all the mistakes listed here. Always
remember that your team members are people first and
programmers second. You can expect them to be
temperamental, inconsistent, proud, undisciplined and

cynical – perhaps all in the same day. Which is to say
they are flawed and imperfect, just like you and everyone
else. So cut them some slack. Everyone has good and bad
days, strengths and weaknesses; so tolerance is the order
of the day.
If someone breaks the build, it’s no big deal. If a
regression is introduced, learn something by finding out
how it got there, but don’t get upset over it or attempt to
assign blame. If a deadline is missed, stand back from
the immediate situation and appreciate that in the grand
scheme of things, it really doesn’t matter. Mistakes
happen and you should expect your colleagues to make
many, as you will surely make many yourself.

References
1. Becoming A Technical Leader – G. M. Weinberg,
Dorset House, 1986
2. Facts And Fallacies of Software Engineering -
Robert L. Glass, Addison-Wesley, 2003

 


 

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