diff --git a/src/components/GanttChart.vue b/src/components/GanttChart.vue
index 3c880b793..f00febe0a 100644
--- a/src/components/GanttChart.vue
+++ b/src/components/GanttChart.vue
@@ -72,12 +72,12 @@
             :tabindex="o.tabindex"
             :progression="o.objective.progression"
             :style="objectiveStyle(o)"
-            :active="
-              (activeObjective && activeObjective.id === o.objective.id) ||
-              workbenchObjectives.map((o) => o.id).includes(o.objective.id)
-            "
+            :checkable="workbenchObjectives.length > 0"
+            :checked="workbenchObjectives.map((o) => o.id).includes(o.objective.id)"
+            :active="activeObjective && activeObjective.id === o.objective.id"
             :data-id="o.objective.id"
-            :before-navigate="beforeSelectObjective(o.objective)"
+            :before-navigate="beforeObjectiveNavigate(o.objective)"
+            @toggle="toggleObjective($event, o.objective)"
             @hook:mounted="onObjectiveMounted(o.objective)"
           />
         </div>
@@ -430,41 +430,86 @@ export default {
       window.removeEventListener('mouseup', this.stopDrag);
     },
 
-    beforeSelectObjective(objective) {
+    async selectObjective(objective) {
+      if (
+        !this.workbenchObjectives.length &&
+        this.activeObjective &&
+        objective.id !== this.activeObjective.id
+      ) {
+        // Close currently active objective if next objective is selected for
+        // the workbench
+        const activeObjectiveId = this.activeObjective.id;
+        this.$router.push({ name: 'ItemHome' });
+
+        // Add both objectives to the workbench using `setTimeout` to give the
+        // browser a chance to "catch up" while toggling panes
+        setTimeout(async () => {
+          await Promise.all(
+            [activeObjectiveId, objective.id].map(this.addWorkbenchObjective)
+          );
+          this.scrollToObjective(objective);
+        });
+        return;
+      }
+
+      // Add selected objective to workbench
+      await this.addWorkbenchObjective(objective.id);
+      this.scrollToObjective(objective);
+    },
+
+    async unselectObjective(objective) {
+      // Remove objective from workbench
+      await this.removeWorkbenchObjective(objective.id);
+
+      // Set next workbench objective as active if available
+      if (this.activeObjective && this.activeObjective.id === objective.id) {
+        if (this.workbenchObjectives.length) {
+          this.$router.replace({
+            name: 'ObjectiveHome',
+            params: { objectiveId: this.workbenchObjectives[0].id },
+          });
+        } else {
+          this.$router.push({ name: 'ItemHome' });
+        }
+      }
+    },
+
+    beforeObjectiveNavigate(objective) {
       return async (event) => {
-        if (event.metaKey) {
-          event.preventDefault();
+        const modifierKey = event.metaKey || event.altKey;
 
-          if (this.activeObjective && objective.id !== this.activeObjective.id) {
-            // Add currently active objective to workbench if the next objective
-            // is selected with the modifier key.
-            await this.addWorkbenchObjective(this.activeObjective.id);
-          }
+        if (!modifierKey && !this.workbenchObjectives.length) {
+          return;
+        }
 
-          if (!this.workbenchObjectives.find((o) => o.id === objective.id)) {
-            await this.addWorkbenchObjective(objective.id);
-            this.scrollToObjective(objective);
-
-            if (this.activeObjective && objective.id !== this.activeObjective.id) {
-              await this.$router.replace({
-                name: 'ObjectiveHome',
-                params: { objectiveId: objective.id },
-              });
-            }
-          } else {
-            await this.removeWorkbenchObjective(objective.id);
+        // Prevent default link navigation when selecting/unselecting
+        // objectives for the workbench
+        event.preventDefault();
+
+        if (!this.workbenchObjectives.find((o) => o.id === objective.id)) {
+          await this.selectObjective(objective);
+
+          // Replace any active objective with the one newly selected
+          if (this.activeObjective && objective.id !== this.activeObjective.id) {
+            await this.$router.replace({
+              name: 'ObjectiveHome',
+              params: { objectiveId: objective.id },
+            });
           }
-        } else if (
-          this.workbenchObjectives.length &&
-          !this.workbenchObjectives.find((o) => objective.id === o.id)
-        ) {
-          // Clear the workbench if an object is selected with the modifier key
-          // and it is not currently listed.
-          this.clearWorkbenchObjectives();
+        } else {
+          await this.unselectObjective(objective);
         }
       };
     },
 
+    async toggleObjective(checked, objective) {
+      if (checked) {
+        await this.selectObjective(objective);
+      } else {
+        await this.unselectObjective(objective);
+      }
+    },
+
     onObjectiveMounted(objective) {
       // Scroll to active objective when first mounted in the timeline.
       if (objective.id === this.activeObjective?.id) {
@@ -489,10 +534,20 @@ export default {
     },
 
     async periodObjectivesToWorkbench() {
-      this.periodObjectives
-        .filter((po) => !this.workbenchObjectives.map((o) => o.id).includes(po.id))
-        .map((o) => o.id)
-        .forEach(this.addWorkbenchObjective);
+      // Reset and add all objectives within current period to the workbench
+      await this.clearWorkbenchObjectives();
+
+      if (!this.periodObjectives.length) {
+        return;
+      }
+
+      this.periodObjectives.map((o) => o.id).forEach(this.addWorkbenchObjective);
+
+      // Set first workbench objective as active
+      await this.$router.replace({
+        name: 'ObjectiveHome',
+        params: { objectiveId: this.periodObjectives[0].id },
+      });
 
       this.$nextTick(() => {
         if (this.$refs.period) {
diff --git a/src/components/OkrLinkCard.vue b/src/components/OkrLinkCard.vue
index 86b5cdf45..9ee24cf34 100644
--- a/src/components/OkrLinkCard.vue
+++ b/src/components/OkrLinkCard.vue
@@ -5,6 +5,7 @@
         'okr-link-card',
         {
           'okr-link-card--active': isExactActive || active,
+          'okr-link-card--checked': checked,
           'okr-link-card--compact': compact,
         },
       ]"
@@ -12,15 +13,18 @@
       @click="activate($event, navigate)"
     >
       <div class="okr-link-card__inner">
-        <pkt-tag
-          v-if="!compact"
-          text-style="normal-text"
-          skin="yellow"
-          size="small"
-          class="okr-link-card__owner"
-        >
-          {{ activeItem.name }}
-        </pkt-tag>
+        <div v-if="!compact" class="okr-link-card__header">
+          <input
+            v-if="checkable"
+            type="checkbox"
+            class="pkt-form-check-input"
+            :checked="checked"
+            @click.stop="$emit('toggle', $event.target.checked)"
+          />
+          <pkt-tag text-style="normal-text" skin="yellow" size="small">
+            {{ activeItem.name }}
+          </pkt-tag>
+        </div>
 
         <span class="okr-link-card__title pkt-txt-14">
           {{ title }}
@@ -62,6 +66,14 @@ export default {
       type: Boolean,
       default: false,
     },
+    checked: {
+      type: Boolean,
+      default: false,
+    },
+    checkable: {
+      type: Boolean,
+      default: false,
+    },
     compact: {
       type: Boolean,
       default: false,
@@ -117,7 +129,10 @@ export default {
     padding: 1rem;
   }
 
-  &__owner {
+  &__header {
+    display: flex;
+    gap: 0.5rem;
+    align-items: center;
     white-space: nowrap;
   }
 
@@ -125,10 +140,13 @@ export default {
     text-wrap: balance;
   }
 
-  &--active {
+  &--active,
+  &--checked {
     color: var(--color-hover);
-    background-color: var(--color-blue-5);
     border: 2px solid var(--color-hover);
   }
+  &--active {
+    background-color: var(--color-blue-5);
+  }
 }
 </style>
diff --git a/src/components/drawers/EditObjective.vue b/src/components/drawers/EditObjective.vue
index 2fa901769..5773c663e 100644
--- a/src/components/drawers/EditObjective.vue
+++ b/src/components/drawers/EditObjective.vue
@@ -109,7 +109,7 @@
 </template>
 
 <script>
-import { mapActions, mapState } from 'vuex';
+import { mapState } from 'vuex';
 import { isEqual } from 'date-fns';
 import { db } from '@/config/firebaseConfig';
 import { formattedPeriod } from '@/util/okr';
@@ -220,7 +220,6 @@ export default {
 
   methods: {
     formattedPeriod,
-    ...mapActions('okrs', ['setActiveObjective', 'addWorkbenchObjective']),
 
     getCurrentDateRange() {
       if (this.thisObjective.startDate && this.thisObjective.endDate) {
diff --git a/src/components/layout/PaneLayout.vue b/src/components/layout/PaneLayout.vue
index 0d23919f9..bae8965e8 100644
--- a/src/components/layout/PaneLayout.vue
+++ b/src/components/layout/PaneLayout.vue
@@ -75,10 +75,10 @@ export default {
 }
 
 .slide-fade-enter-active {
-  transition: all 0.3s ease;
+  transition: all 0.4s ease;
 }
 .slide-fade-leave-active {
-  transition: all 0.1s cubic-bezier(1, 0.5, 0.8, 1);
+  transition: none;
 }
 .slide-fade-enter,
 .slide-fade-leave-to {
diff --git a/src/components/panes/WorkbenchPane.vue b/src/components/panes/WorkbenchPane.vue
index 0e57847ef..f380b5eb2 100644
--- a/src/components/panes/WorkbenchPane.vue
+++ b/src/components/panes/WorkbenchPane.vue
@@ -28,7 +28,7 @@
           variant="icon-only"
           icon-name="minus-circle"
           skin="tertiary"
-          @onClick="removeObject(objective)"
+          @onClick="removeObjective(objective)"
         />
       </div>
     </div>
@@ -66,7 +66,7 @@ export default {
   methods: {
     ...mapActions('okrs', ['removeWorkbenchObjective', 'clearWorkbenchObjectives']),
 
-    async removeObject(objective) {
+    async removeObjective(objective) {
       await this.removeWorkbenchObjective(objective.id);
 
       // Set next objective as active or unset current if removed.
@@ -84,9 +84,6 @@ export default {
 
     async close() {
       await this.clearWorkbenchObjectives();
-      if (this.$route.name !== 'ItemHome') {
-        this.$router.push({ name: 'ItemHome' });
-      }
     },
   },
 };
@@ -108,7 +105,7 @@ export default {
     top: -1rem;
     right: -1rem;
     height: 2rem;
-    padding: 0 0.25rem;
+    padding: 0 0.25rem !important;
     color: var(--color-grayscale-40);
     background-color: var(--color-white);
     border-radius: 50%;
diff --git a/src/views/Item/ItemOKRs.vue b/src/views/Item/ItemOKRs.vue
index 385797caa..7ad4a3f9d 100644
--- a/src/views/Item/ItemOKRs.vue
+++ b/src/views/Item/ItemOKRs.vue
@@ -166,7 +166,7 @@ export default {
     ...mapActions('okrs', [
       'setActiveObjective',
       'setActiveKeyResult',
-      'clearWorkbenchObjectives',
+      'addWorkbenchObjective',
     ]),
 
     async setData() {
@@ -247,7 +247,7 @@ export default {
       this.$router.push({ name: 'ObjectiveHome', params: { objectiveId: objective.id } });
 
       if (this.workbenchObjectives.length) {
-        await this.addWorkbenchObjective(objective);
+        await this.addWorkbenchObjective(objective.id);
       }
     },
   },