Prioritizing tasks, or planning for them, is one of the biggest strengths of leaders. They are tasked with re-architecting organizations, and they develop comprehensive plans to achieve the same. They also ensure they execute the plan to the best of their abilities, but others get stuck in the planning phase.

1. Planning
To stick to the plan

2. Index
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The planning fallacy 03
1.
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Reasons for incorrect planning 04
2.
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Ways to stick to a plan 07
3.
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A blueprint to plan better 09
4.
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About Upraise 11
5.
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3. 1. The planning fallacy
unreliable
with their estimates regarding time
Prioritizing tasks, or planning for them, is one of the biggest strengths of
leaders. They are tasked with re-architecting organisations, and they develop
comprehensive plans to achieve the same. They also ensure they execute the
plan to the best of their abilities, but others get stuck at the planning phase.
It is a more common phenomenon that most realize. Individuals are
, as research suggests. It is a deeper
investigation of a psychological phenomenon called “delay discounting,” in
which people tend to lessen the importance of responsibilities in future, and
expect to have more time – and promise unrealistic deadlines. Subsequently,
they end up exceeding that deadline by a couple of days. While the task may
have been completed, the delay can cause many problems that could have
been avoided if the deliverables were planed meticulously.
The idea of planning as we know it is bound to fail, because people expect
future to be perfect. With the addition of other factors, like lack of information,
dependence on other teams, or something else – the planning process needs to
be relooked at closely in order to Re-architect Work.
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4. 2. Reasons for incorrect
planning
The phrase ‘bad at planning’ does not explain exactly what is the ‘bad’ part. This
can cause even good contributors and leaders look mediocre. The reasons for
the failure of the plan can be multiple and varied, and they don’t always follow
a pattern. Here are a few:
Lack of organisational skills
future of jobs report
Lack of organisational skills can vary from misplacing a note or a pen, to
forgetting about meetings. Identifying a pattern in these mistakes and using
tools to organize a schedule, can help.
While being organized sounds simple and easy enough, it isn’t. That’s why
organisational skills are one of the most important aspects of hiring at a
managerial level, according to the by World Economic
Forum. The skills that organisations consider important are planning, critical
thinking, attention to detail and conflict management.
Developing these skills can help employees contribute better, compartmentalize
better, and have a better work/life balance.
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5. Page 5
2. Reasons for incorrect planning
Types of Organizational Skills Emoloyers Seek
Physical Organization
Administrative
Creative Thinking
Effectiveness
Productivity
Planning
Analyzing Issues
Decision Making
Project Management
Strategy Planning
Teamwork
Collaboration
Delegation
Goal Setting
Group Leadership
Insufficient information of variables involved
Like Chinese whispers, a lot of information gets lost between teams, even if
everything is documented on emails. Often, this leads to teams – or individual
employees – to work with limited information. This can happen because of
various factors, like deadlines looming close by, urgent security related updates,
or something else. Not only this is a waste of precious time, it also leads to
frustration and employees might not be interested to work at all.
Managers should ensure everyone in the team is on the same page, and keep
all channels of communication open. Regular meetings with the teams and
providing constant feedback, is essential to the organized execution of the
project.

6. Page 6
2. Reasons for incorrect planning
Lack of focus and resources
When the objectives and goals are ambiguous, the efforts by employees trying
to achieve those goals will appear muddled too. That’s why it is essential for
managers to identify the resources necessary for the project, and figure out
ways to enable their team with the same.
Not willing to follow through
Feedback puts employees on guard, because the expectation is to receive it
once a year – and that too from the lens of ‘how to improve performance’.
Receiving constant feedback can prove unnerving to some employees, and
managers need to handle it with utmost care.
Overestimation and under-delivery
Hofstadter's law
People tend to consider the best case scenarios when they’re estimating time,
and invariably it falls short. Managers can help employees by asking them
specific questions about the feasibility of the timelines, the assumptions made
to arrive at the timeline, other needs that might pop up during the project, and
so on. Managers and their team members should get all the requirements out in
the open before committing on the timeline.
Even after taking everything into account, it is prudent to add an acceptable
amount of buffer time in the estimation – as demanded by pay heed to the
, which states "It always takes longer than you expect, even
when you take into account Hofstadter's Law."

7. 3. Ways to stick to a plan
Like all important things, the act of planning requires a little bit of planning too.
The pointers below highlight the action items that can help in improving the
planning phase.
Analyze strengths and weaknesses
Carrying out an assessment of existing strengths and weaknesses using a
SWOT analysis, helps employees and managers to identify the areas they can
contribute better, and the areas they need help. Armed with this information, an
employee can them work with their manager to create an upskilling schedule.
Accept the difficulty
The magnitude of tasks sometimes has a paralysing effect on people, and they
tend to avoid work by getting distracted. In such cases, breaking big projects
into smaller bite-able chunks can help to put the situation in perspective.
Once the project is broken down into smaller parts, employees can start
working on the easiest of the chunks and take it from there. Even if they hit a
snag, rest of the work that has already been accomplished gives them a sense
of confidence to tackle the bigger tasks. Managers can then help the employee
by discussing the matter, and come up with a better solution.
Find systems that work
Mimicking processes that worked for other organisations, can prove detrimental
in the long run. Instead, finding processes that are more suited for the
employees’ skills and capabilities can help them perform better. Someone with
a strong tendency toward visuals, can be helped to find a way to organize via
sticky notes, whiteboards or mindmaps, for example.
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8. Page 8
3. Ways to stick to a plan
Always aiming for 100%
All-or-Nothing thinking can wreak havoc on personal growth, work and on
attempts to shift old thought patterns. Instead of viewing learning as a
continuous process, where improvement counts and every day matters,
employees see it as a destination that will lead to a rewarding corporate
journey.
Also, being resilient is essential – as the deviations from the plan are fairly
normal, and thinking on the feet is a necessity.
Borrow ideas from experts
Asking for advice from people who have exceptional planning and
organisational skills, or just simply observing how they go about their work, is a
good way to understand the proceedings. Trying different techniques that help
in time management can be of help too, because these trials help people
understand the aspects that don’t work – and then the process can be
improved.
One important pointer while learning on one’s own, is to not target mastery in
the subject or activity in a short span of time. Not only will this put the employee
under undue stress, but can lead to errors which can hamper the employee’s
confidence.

9. 4. A blueprint to plan better
The techniques above help in identifying the weak areas in planning, but
addressing them all at once can be intimidating.
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Make new behaviours fit in the routine.
Simplifying the behaviour to fit in the current routing is the best way
to ensure the plan works. For example, a person who is unreliable with
replying to mails can set aside a 15-minute window in the morning to
sift through the mails after the morning cup of coffee.
1
Use the right tools.
Having the proper tool to get the task done also cuts down the barrier
to start. The tool here can be a product or a solution to be provided
by another team, that helps in the current project.
3
Get help whenever needed.
The benefit of working in a team, is that there is a ready group of
people willing to help finish the task. Managers and other leaders can
help in identifying a better way of execution, or help in upskilling.
4
Sort everything by how they’re used.
Having important project-related files easily accessible means not
looking for them when they’re needed. It brings down the barrier to
start drastically.
2
Evaluate often.
Getting constant feedback must always be the part of the plan, as it
allows for iterative development. Also, the chances of errors getting
caught are high, ensuring in better completion of projects.
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4. A blueprint to plan bet ter
Planning is a skill, and skills are mastered over a long period of time.
Understanding this simple statement can save hundreds of hours of self-doubt
and trying various short-cuts (and failing). Knowing that the journey of mastery
will take long, is the first step; Taking a step back and trying to identify potential
fault lines in the plan is the next. But the most important aspect of planning is
practicing self-compassion, instead of getting frustrated when mistakes
happen.

11. Page 11
No better place than JIRA to find context
No separate system, rapid adoption
Connect execution with strategy
About UpRaise
UpRaise is the only context aware, full stack app that seamlessly integrates with
daily workflows of software development teams. Its “Re-architect Work”
principle guides teams towards excellence through improved overall efficiency
of people operations, better alignment to organisation’s larger goals, increased
engagement and improved transparency.
UpRaise helps organisations achieve operational and intellectual excellence
with Employee Success, a JIRA-based comprehensive Employee Performance
Management platform. Natively developed for JIRA as a plugin, Employee
Success includes enterprise grade features such as Objectives Management,
Continuous Feedback & Performance Reviews. Other UpRaise solutions like
Employee Garrison and Upraise People, simplify employee management. They
enable management of employee records, leaves, OKRs, feedback & reviews,
and more – within Jira.